Aldehyde compound, its production method, and fragrance composition

Abstract

Provided are: a novel aldehyde compound which is useful as a fragrance, a compound perfume material or a starting material therefor; a method for producing the same; a fragrance composition containing said compound as an active ingredient; and the use of said compound as a fragrance. The compound is represented by formula (1). (In formula (1), R is a hydrogen atom or a methyl group.)

Description

[Technical field]

[0001] The present invention relates to a novel first aldehyde compound useful as a fragrance and a method for producing the same, as well as a fragrance composition containing the aldehyde compound, and further to a second aldehyde compound useful as a raw material for the first aldehyde compound. [Background technology]

[0002] Compounds having an aroma or flavor are extremely useful as fragrance ingredients, and alkylbenzaldehydes and their derivatives have traditionally been attracting attention for use in fragrance applications and as fragrance raw materials. Patent Document 1 describes that 3-(4-(sec-butyl)-2-methylphenyl)propanal and 3-(4-isobutyl-2-methylphenyl)-2-methylpropanal have an odor. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2018-138550 A Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention aims to provide a novel first aldehyde compound useful as a fragrance and blended fragrance material, a method for producing the same, a fragrance composition containing the first aldehyde compound as an active ingredient, and use of the compound as a fragrance. Another objective of the present invention is to provide a novel second aldehyde compound useful as a raw material for the first aldehyde compound. [Means for solving the problem]

[0005] The present inventors synthesized various compounds and investigated their odors, and discovered that a specific aldehyde compound has a lily of the valley-like odor, which led to the completion of the present invention.

[0006] The present invention relates to the following <1> ~ <6> to provide. <1> A compound represented by the following formula (1):

[0007] [ka] (In formula (1), R is a hydrogen atom or a methyl group.)

[0008] <2> R is a hydrogen atom; <1> The compound according to claim 1, <3> <1> or <2> A fragrance composition comprising the compound described in claim 1. <4> <1> or <2> 2. Use of the compound according to claim 1 as a fragrance. <5> A compound represented by the following formula (2):

[0009] [ka]

[0010] <6> A method for producing a compound represented by formula (1), comprising the steps of: subjecting a compound represented by formula (2) to aldol condensation with acetaldehyde or propionaldehyde to obtain a compound represented by formula (3); and hydrogenating the compound represented by formula (3) to obtain a compound represented by formula (1), in this order.

[0011] [ka]

[0012] [ka] (In formula (3), R is a hydrogen atom or a methyl group.)

[0013] [Chemical formula] (In formula (1), R is a hydrogen atom or a methyl group.) [Advantages of the Invention]

[0014] According to the present invention, it is possible to provide a novel first aldehyde compound useful as a fragrance and a fragrance ingredient material, a method for producing the same, a fragrance composition containing the first aldehyde compound as an active ingredient, and the use of the compound as a fragrance. Further, according to the present invention, it is possible to provide a novel second aldehyde compound useful as a raw material for the first aldehyde compound. [Modes for Carrying Out the Invention]

[0015] Hereinafter, the present invention will be described using embodiments. In the following description, the description of "A to B" indicating a numerical range represents "A or more and B or less" (when A < B), or "A or less and B or more" (when A > B). That is, it represents a numerical range including the endpoints A and B. Also, parts by mass and mass% are synonymous with parts by weight and weight%, respectively.

[0016] [Compound represented by formula (1)] The first aldehyde compound of the present invention is represented by the following formula (1). [Chemical formula] (In formula (1), R is a hydrogen atom or a methyl group.)

[0017] In formula (1), R is a hydrogen atom or a methyl group. Among these, from the viewpoint of aroma properties, a hydrogen atom is preferred.

[0018] The aldehyde compound represented by formula (1) has an asymmetric carbon when R is a methyl group. In that case, the aldehyde compound may have only one of the optical isomers, or may be a mixture containing a plurality of optical isomers in any ratio.

[0019] The compound represented by formula (1) is a novel compound. The first aldehyde compound of the present invention represented by formula (1) is useful as a fragrance and blended fragrance material, and has a lily of the valley-like odor, and in addition, also has white floral, aldehyde, green, and other odors.

[0020] The compound represented by formula (1) is useful as a fragrance since it has an excellent fragrance by itself as described below. Moreover, fragrances are generally not used alone, but are often used as blended fragrances (fragrance compositions) in which multiple fragrances are blended according to a purpose. The first aldehyde compound of the present invention is useful as a fragrance (also called a "blended fragrance material") to be blended in a blended fragrance (fragrance composition). As a fragrance, the compound represented by formula (1) may be used alone or in combination of two or more. In addition, the compound represented by formula (1) of the present invention does not exclude the inclusion of small amounts of impurities, by-products, contaminants, etc., within the scope that does not impair the effects of the present invention. As described above, the compound represented by formula (1) has a lily of the valley scent as well as a white floral, aldehyde, green or other scent, and is also excellent in diffusibility. The compound represented by formula (1) of the present invention may be used alone as a fragrance to impart an aroma or flavor to various cosmetics, health and hygienic materials, medicines, daily necessities, foods, etc., or the compound represented by formula (1) of the present invention may be mixed with other blended fragrance materials, etc. to prepare a fragrance composition (blended fragrance) described below, which is then blended into various products to impart an aroma or flavor. Among these, from the viewpoint of obtaining the desired aroma or flavor, it is preferable to blend the compound of the present invention as a blended fragrance material into a fragrance composition, and blend the fragrance composition into a product to impart a fragrance.

[0021] [Fragrance composition] The fragrance composition (blended fragrance) of the present invention contains a compound represented by formula (1) (the first aldehyde compound of the present invention) as an active ingredient. There are no particular limitations on the composition as long as it contains at least one type of the first aldehyde compound of the present invention, and it may contain two types of the first aldehyde compound of the present invention. The fragrance imparts at least one of an aroma and a flavor (hereinafter, "at least one of an aroma and a flavor" is also referred to as "aroma, etc."). The fragrance composition of the present invention is not limited as long as it contains the first aldehyde compound of the present invention as an active ingredient, and the other ingredients are not particularly limited. It is preferable that the fragrance composition further contains other blended fragrance materials (hereinafter, also referred to as "conventional fragrance"). It should be noted that a "fragrance composition (blended fragrance)" is a composition which imparts a fragrance or the like when added to various cosmetic products, medicines, foods, beverages, etc., or a composition which can be used as such in perfumes, etc., and which may contain additives such as solvents as necessary in addition to conventional fragrances. The amount of the first aldehyde compound of the present invention to be blended varies depending on the type of the first aldehyde compound of the present invention, the type of the desired fragrance, etc., and the intensity of the fragrance, etc., but the amount of the first aldehyde compound of the present invention represented by formula (1) in the fragrance composition is preferably 0.001 mass% or more, more preferably 0.01 mass% or more, even more preferably 0.1 mass% or more, and is preferably 90 mass% or less, more preferably 70 mass% or less, and even more preferably 50 mass% or less.

[0022] The conventional fragrance is not particularly limited as long as it is a conventionally known fragrance component, and a wide range of fragrances can be used. For example, the following can be selected and used alone or in any mixture of two or more kinds in any ratio: For example, hydrocarbons such as limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene; linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyl linalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, β-phenylethyl alcohol, benzyl alcohol, phenylhexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, 1-(2-t-butylcyclohexyloxy)-2-butanol, 4- Alcohols such as isopropylcyclohexanemethanol, 4-t-butylcyclohexanol, 4-methyl-2-(2-methylpropyl)tetrahydro-2H-pyran-4-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, isocamphylcyclohexanol, and 3,7-dimethyl-7-methoxyoctan-2-ol; phenols such as eugenol, thymol, and vanillin;Linalyl formate, citronellyl formate, geranyl formate, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyr acetate, bornyl acetate, isobornyl acetate, ot-butylcyclohexyl acetate, pt-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, styraryl acetate, cinnamyl acetate, dimethyl benzyl acetate, Dimethylbenzylcarbinyl acetate, 3-pentyltetrahydropyran-4-yl acetate, citronellyl propionate, tricyclodecenyl propionate, allyl cyclohexyl propionate, ethyl 2-cyclohexyl propionate, benzyl propionate, citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenyl isobutyrate, methyl 2-nonenoate, methyl benzoate, benzyl benzoate, methyl cinnamate, methyl salicylate, n-hexyl salicylate esters such as cis-3-hexenyl salicylate, geranyl tiglate, cis-3-hexenyl tiglate, methyl jasmonate, methyl dihydrojasmonate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl methylphenylglycidate, methyl anthranilate, and flutate; n-octanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, dimethyltetrahydrobenzaldehyde, and the like. aldehydes such as cinnamic aldehyde, 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 2-cyclohexylpropanal, p-butyl-α-methylhydrocinnamic aldehyde, p-isopropyl-α-methylhydrocinnamic aldehyde, p-ethyl-α,α-dimethylhydrocinnamic aldehyde, α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, piperonal, and α-methyl-3,4-methylenedioxyhydrocinnamic aldehyde;Methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2-heptanone, amylcyclopentanone, 3-methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one, methylcyclopentenolone, rose ketone, γ-methylionone, α-ionone, carvone, menthone, camphor, nootkatone, benzylacetone, anisylacetone, methyl β-naphthyl ketone, 2,5-dimethyl-4-hydroxy-3(2H)-furano Ketones such as acetaldehyde, maltol, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, muscone, civetone, cyclopentadecanone, and cyclohexadecenone; acetals and ketals such as acetaldehyde ethyl phenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glycerin acetal, and ethyl acetoacetate ethylene glycol ketal; anethole, Ethers such as β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, 1,8-cineole, racemic or optically active dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan; nitriles such as citronellyl nitrile; γ-nonalactone, γ-undecalactone, σ-decalactone, γ-jasmolactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, and ambrette. lactones such as ethylene brassylate, 11-oxahexadecanolide, etc.; other fragrance substances such as natural essential oils and natural extracts such as orange, lemon, bergamot, mandarin, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, sandalwood, vetiver, patchouli, labdanum, etc.;

[0023] The fragrance composition may also contain, as components other than the blended fragrance materials, surfactants such as polyoxyethylene lauryl sulfate ether; solvents such as dipropylene glycol, diethyl phthalate, ethylene glycol, propylene glycol, methyl myristate, and triethyl citrate; antioxidants such as BHT (di-tert-butylhydroxytoluene) and vitamin E (tocopherol); colorants, etc., and it is preferable that the fragrance composition contains at least an antioxidant.

[0024] The first aldehyde compound of the present invention represented by formula (1) has a lily of the valley scent as well as a white floral, aldehyde, green or other scent. Therefore, when combined with a conventional fragrance, it can impart a natural white floral, aldehyde or green scent in addition to the lily of the valley scent. Therefore, it is useful for imparting a scent, etc. by adding it to various cosmetics, health and hygienic materials, as well as medicines, daily necessities, foods and the like.

[0025] Examples of products to which the fragrance composition containing the first aldehyde compound of the present invention represented by formula (1) can be added in order to impart fragrance and improve the fragrance of the target product include various products such as cosmetics, health and hygiene materials, miscellaneous goods, beverages, foods, quasi-drugs, and pharmaceuticals, and examples of such products include fragrance products such as perfumes and colognes; shampoos, rinses, hair tonics, hair creams, mousses, gels, pomades, sprays, and other hair cosmetics; lotions, beauty essences, creams, milky lotions, packs, and foundations. It can be used as a component to impart fragrance, etc. to skin cosmetics such as lotions, face powders, lipsticks, and various types of make-up; dishwashing detergents, laundry detergents, softeners, disinfectant detergents, deodorizing detergents, room air fresheners, furniture care, glass cleaners, furniture cleaners, floor cleaners, disinfectants, insecticides, bleaches, germicides, repellents, and other various health and hygiene detergents; toothpaste, mouthwash, bath additives, antiperspirant products, perm solution, and other quasi-drugs; miscellaneous goods such as toilet paper and tissue paper; pharmaceuticals, etc.; and foods, etc.

[0026] The blending amount of the fragrance composition in the above-mentioned product is not particularly limited, and can be selected from a wide range depending on the type, properties, and sensory effect of the product to be scented, etc. For example, it is 0.00001% by mass or more, preferably 0.0001% by mass or more, and more preferably 0.001% by mass or more, and in the case of fragrances such as perfume, it may be 100% by mass, but is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or less.

[0027] [Compound represented by formula (2)] The second aldehyde compound of the present invention is represented by the following formula (2).

[0028] [ka]

[0029] The compound represented by the above formula (2) is useful as a synthetic intermediate (or synthetic raw material) for the first aldehyde compound of the present invention described above. In addition to the compound represented by formula (1), it is also expected that the compound represented by formula (2) can be used to synthesize other compounds useful as fragrances. A method for synthesizing the compound represented by formula (1) and a method for using the compound represented by formula (2) as a synthetic intermediate (or synthetic raw material) for the compound represented by formula (1) will be described later. In the present invention, in synthesizing the compound represented by formula (1), it is not excluded that the compound represented by formula (2) contains a small amount of impurities, by-products, contaminants, etc., within a range that does not impair the effects of the present invention.

[0030] <Method for producing the compound represented by formula (2)> In the present invention, the method for producing the compound represented by formula (2) is not particularly limited, and examples thereof include a method in which 3-neopentyltoluene is reacted with carbon monoxide in the presence of triflic acid (trifluoromethanesulfonic acid) under pressurized conditions. However, it is preferable to produce the compound by reacting 3-neopentyltoluene with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride. Specifically, it is expressed by the following formula.

[0031] [ka]

[0032] In the above reaction, the 4- and 6-positions of 3-neopentyltoluene are susceptible to formylation, and it is preferable to improve the regioselectivity to perform formylation at the 6-position. As described below, the regioselectivity of formylation varies depending on the amounts of hydrogen fluoride and boron trifluoride relative to 3-neopentyltoluene, the carbon monoxide pressure, the reaction time, the reaction temperature, and the like, and the regioselectivity can be improved by optimizing these.

[0033] Hydrogen fluoride (HF) also functions as a solvent for the reaction. From the viewpoint of reactivity, hydrogen fluoride is preferably substantially anhydrous. Here, "substantially anhydrous" means that the water content is 5% by mass or less, preferably 1% by mass or less, more preferably 0.1% by mass or less. The molar ratio of hydrogen fluoride to 3-neopentyltoluene (hydrogen fluoride / 3-neopentyltoluene) is preferably 1.5 or more, more preferably 3.0 or more, and even more preferably 5.0 or more, from the viewpoints of reactivity with carbon monoxide and suppression of side reactions, and is preferably 30.0 or less, more preferably 20.0 or less, and even more preferably 12.0 or less, from the viewpoints of economy and production efficiency.

[0034] From the viewpoint of proceeding with formylation regioselectively, the molar ratio of boron trifluoride (BF3) to 3-neopentyltoluene (boron trifluoride / 3-neopentyltoluene) is preferably 0.1 or more, more preferably 0.5 or more, even more preferably 1.0 or more, still more preferably 1.2 or more, and is preferably 5.0 or less, more preferably 3.0 or less, and even more preferably 2.0 or less.

[0035] The temperature at which carbon monoxide is reacted during the reaction is preferably −50° C. or higher, more preferably −40° C. or higher, and is preferably 30° C. or lower, more preferably 10° C. or lower, and even more preferably 5° C. or lower, from the viewpoints of improving reactivity, suppressing side reactions, and improving selectivity of the position at which a formyl group is introduced. The reaction between 3-neopentyltoluene and carbon monoxide is preferably carried out under pressure. From the viewpoint of improving reactivity and suppressing side reactions, the pressure during the reaction is, in terms of carbon monoxide partial pressure, preferably 1.0 MPaG or more, more preferably 1.5 MPaG or more, even more preferably 1.8 MPaG or more, and is preferably 3.0 MPaG or less, more preferably 2.5 MPaG or less, even more preferably 2.2 MPaG or less.

[0036] In the present invention, the reaction time is not particularly limited, but from the viewpoints of allowing the reaction to proceed sufficiently, suppressing side reactions and decomposition of the product, and producing efficiently, the reaction time is preferably 10 minutes or more, more preferably 20 minutes or more, even more preferably 30 minutes or more, and is preferably 24 hours or less, more preferably 12 hours or less, even more preferably 5 hours or less.

[0037] The production method of the present invention may be carried out in the presence of a solvent. The solvent to be used is not particularly limited as long as it has good solubility for the reaction raw materials and is inactive against hydrogen fluoride and boron trifluoride. Examples of the solvent include saturated aliphatic hydrocarbons such as hexane, heptane, and decane, aromatic hydrocarbons such as benzene and toluene, and halogenated aliphatic hydrocarbons such as chloroform, methylene chloride, and dichloroethane. These solvents may be used alone or in combination of two or more. The amount of the solvent used is not particularly limited, and may be appropriately selected from the viewpoints of reaction uniformity, reaction rate, and solvent removal. In the present invention, since hydrogen fluoride present during the reaction also functions as a solvent, it is not necessary to use a solvent.

[0038] The above reaction may be carried out in any manner, such as batchwise, semi-batchwise or continuous manner. From the viewpoint of the recovery and reuse of the catalyst and production efficiency, the reaction is preferably carried out in a continuous manner. The apparatus used in the production method is a reaction apparatus capable of sufficiently mixing the liquid phase and the gas phase under pressure while controlling the temperature. For example, in a continuous reaction, hydrogen fluoride and boron trifluoride are first charged into a reactor equipped with a stirrer, the contents are stirred, the liquid temperature is set to a suitable temperature, and the temperature is kept constant. After that, the pressure is increased to a suitable reaction pressure using carbon monoxide, and a state is created in which carbon monoxide can be supplied so as to keep the pressure constant. Thereafter, a semi-batch reaction is carried out in which 3-neopentyltoluene dissolved in a solvent is supplied as necessary. Subsequently, the supply of hydrogen fluoride, boron trifluoride, and 3-neopentyltoluene dissolved in a solvent as necessary is started, and the reaction product liquid is continuously withdrawn. After removing hydrogen fluoride and boron trifluoride from the resulting reaction solution containing 2-methyl-4-neopentylbenzaldehyde, the solution can be purified by a conventional method such as distillation, extraction, etc. In order to remove hydrogen fluoride from the reaction solution, the solution may be neutralized with an aqueous sodium hydroxide solution and washed with water.

[0039] The compound represented by the above formula (a) (3-neopentyltoluene) may be synthesized as follows.

[0040] [ka]

[0041] Neopentylbenzene is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to formylate the p-position of the neopentyl group, yielding 4-neopentylbenzaldehyde. Next, the resulting 4-neopentylbenzaldehyde is reduced in the presence of a palladium catalyst to reduce the formyl group to a methyl group. Furthermore, the obtained 4-neopentyltoluene is subjected to an isomerization reaction in the presence of hydrogen fluoride and boron trifluoride, and 3-neopentyltoluene produced by the isomerization reaction is isolated, thereby obtaining 3-neopentyltoluene.

[0042] [Method for producing the compound represented by formula (1)] The compound represented by formula (1) may be produced by any method, for example, a method of brominating 6-position of 3-neopentyltoluene, reacting with allyl alcohol in the presence of a secondary amine and a palladium catalyst, and oxidizing the propanol side chain of the resulting compound, etc. For the above method, see JP2017-533926A. In the present invention, it is preferable to produce the compound represented by formula (1) by the following production method, specifically, the production method having the following steps (i) and (ii) in this order. Step (i): A step of subjecting the compound represented by the above formula (2) to aldol condensation with acetaldehyde or propionaldehyde to obtain a compound represented by the following formula (3): Step (ii): A step of hydrogenating a compound represented by the following formula (3) to obtain a compound represented by the above formula (1):

[0043] [ka] (In formula (3), R is a hydrogen atom or a methyl group.)

[0044] The reaction scheme is shown below.

[0045] [ka] (In the formula, R is a hydrogen atom or a methyl group.)

[0046] <Process (i)> Step (i) is a step of subjecting the compound represented by the above formula (2) to aldol condensation with acetaldehyde or propionaldehyde to obtain the compound represented by the above formula (3). More specifically, it is preferred to react the compound represented by formula (2) with acetaldehyde or propionaldehyde in the presence of a basic compound as a catalyst. Examples of the basic compound used as a catalyst include sodium hydroxide, potassium hydroxide, sodium bicarbonate, and mixtures thereof. The amount of the basic compound is preferably 0.05 equivalents or more, more preferably 0.1 equivalents or more, even more preferably 0.2 equivalents or more, and is preferably 3 equivalents or less, more preferably 1 equivalent or less, even more preferably 0.5 equivalents or less, relative to 1 equivalent of the compound represented by formula (2). The amount of acetaldehyde or propionaldehyde added is preferably 1.0 equivalent or more, more preferably 1.05 equivalent or more, and preferably 1.5 equivalents or less, more preferably 1.1 equivalents or less, relative to 1 equivalent of the compound represented by formula (2). The addition of acetaldehyde or propionaldehyde is preferably carried out stepwise or continuously over time, for example by dropwise addition.

[0047] The above reaction is preferably carried out in a solvent. Examples of the solvent to be used include various water-miscible organic solvents. Specifically, preferred examples include alcohols such as methanol, ethanol, 1-propanol, 2-propanol, tert-butanol, allyl alcohol, ethylene glycol, propylene glycol, and diethylene glycol, and more preferred are methanol, ethanol, 1-propanol, 2-propanol, tert-butanol, ethylene glycol, propylene glycol, and diethylene glycol. The reaction temperature is not particularly limited, but from the viewpoint of reaction rate, it is preferably 0° C. or higher, more preferably 3° C. or higher, and even more preferably 5° C. or higher, and from the viewpoint of suppressing side reactions, it is preferably 50° C. or lower, more preferably 40° C. or lower, and even more preferably 30° C. or lower. The reaction time is not particularly limited as long as the condensation is sufficiently carried out, but is preferably 10 minutes or more, more preferably 30 minutes or more, even more preferably 1 hour or more, and is preferably 24 hours or less, more preferably 12 hours or less, even more preferably 6 hours or less, and even more preferably 3 hours or less.

[0048] The reaction can be stopped by neutralization, for example, by adding an acid such as acetic acid. The method for isolating the compound represented by formula (3) from the reaction solution is not particularly limited, and may be an appropriate combination of separation and extraction operations, chromatography, etc. For example, a low polarity or non-polar organic solvent is added to the reaction solution, the compound represented by formula (3) is transferred to the oil phase, the oil phase obtained is dried, for example, with magnesium sulfate, and the filtrate obtained by filtration is concentrated and further purified by column chromatography, whereby the compound can be isolated.

[0049] <Process (ii)> The step (ii) is a step of hydrogenating the compound represented by the above formula (3) obtained in the step (i) to obtain the compound represented by the above formula (1). The method of hydrogenation is not particularly limited, and can be a known method using a hydrogenation catalyst. The hydrogenation catalyst is not particularly limited, and known catalysts can be used. For example, supported heterogeneous hydrogenation catalysts in which a metal such as Ni, Pt, Pd, Ru, etc. is supported on carbon, silica, alumina, diatomaceous earth, etc.; so-called Ziegler type hydrogenation catalysts which use a transition metal salt such as an organic acid salt or an acetylacetone salt of Ni, Co, Fe, Cr, etc., and a reducing agent such as organoaluminum; and homogeneous hydrogenation catalysts such as so-called organometallic complexes of organometallic compounds such as Ti, Ru, Rh, Zr, etc., can be used.

[0050] From the viewpoint of suppressing reactivity and side reactions, the temperature of the hydrogenation reaction is preferably 0° C. or higher, more preferably 10° C. or higher, and even more preferably 20° C. or higher, and is preferably 200° C. or lower, more preferably 150° C. or lower, and even more preferably 100° C. or lower. The pressure of hydrogen used in the hydrogenation reaction is preferably 0.01 MPaG or more, more preferably 0.03 MPaG or more, even more preferably 0.05 MPaG or more, and preferably 10 MPaG or less, more preferably 3 MPaG or less, even more preferably 1 MPaG or less, and still more preferably 0.5 MPaG or less. The reaction time is not particularly limited, but is preferably 3 minutes or more, more preferably 10 minutes or more, and even more preferably 30 minutes or more, and is preferably 24 hours or less, more preferably 12 hours or less, and even more preferably 8 hours or less.

[0051] The hydrogenation reaction may be carried out in the presence of a solvent. The solvent to be used is not particularly limited as long as it does not inhibit the hydrogenation reaction, and examples thereof include aliphatic hydrocarbons such as pentane, hexane, isopentane, heptane, octane, and isooctane; alicyclic hydrocarbons such as cyclopentane, methylcyclopentane, cyclohexane, methylcyclohexane, and ethylcyclohexane; and aromatic hydrocarbons such as benzene, toluene, ethylbenzene, and xylene. These may be used alone or in combination of two or more.

[0052] The method for isolating and purifying the compound represented by the formula (1) from the reaction solution is not particularly limited, and a known method may be appropriately selected and carried out. Specifically, filtration, chromatography, distillation purification, etc. are exemplified, and these may be appropriately combined for purification.

Examples

[0053] Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.

[0054] <NMR Spectrum Analysis> Apparatus: JEOL JNM-AL-400 400 MHz (manufactured by JEOL) Solvent: deuterated chloroform (CDCl3) Measurement mode: 1 H, 13 C Internal standard substance: tetramethylsilane (TMS)

[0055] <Mass Spectrometry> Apparatus: GCMS-QP2010 Ultra (manufactured by Shimadzu Corporation) Ionization method: EI

[0056] <Fragrance Evaluation> The fragrance of the obtained compound was evaluated by impregnating a filter paper having a width of 8 mm and a length of 15 cm and having a professional panelist smell it.

[0057] [Examples] In the following examples, when the synthesis amount was insufficient as a raw material for the next synthesis, the necessary amount was synthesized by repeating the same synthesis a plurality of times. <Synthesis of 4-neopentylbenzaldehyde> A 500 mL autoclave equipped with a knuckle drive type stirrer, three inlet nozzles at the top, and one outlet nozzle at the bottom and capable of controlling the internal temperature by a jacket was used as a formylation reactor. Hydrogen fluoride 134.2 g (6.71 mol) was charged into the autoclave cooled to -25°C by flowing a refrigerant through the jacket. Thereafter, while stirring and adjusting the temperature so that it did not exceed -25°C, 70.6 g (1.04 mol) of boron trifluoride was added. After the boron trifluoride was added, the temperature inside the autoclave was kept at -25°C, while the pressure was increased to 2 MPaG with carbon monoxide, and 100.0 g (0.67 mol) of neopentylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added. After stirring for 90 minutes while maintaining a temperature of -25°C and a pressure of 2MPaG, the reaction mixture in the autoclave was drained into ice water. The drained liquid was thoroughly shaken and the oil layer was separated. The oil layer was neutralized and washed with water, and then distilled and purified (131°C, 15 Torr) to obtain 87.5g (0.50mol) of 4-neopentylbenzaldehyde as a colorless, transparent liquid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained 4-neopentylbenzaldehyde are as follows.

[0058] [4-Neopentylbenzaldehyde] 1 H NMR (400 MHz, CDCl3) δ 0.92 (9H, s), 2.58 (2H, s), 7.28-7.30 (2H, d, J = 8.0Hz), 7.78-7.80 (2H, d, J = 8.0Hz), 9.99 (1H, s) 13 C NMR (100 MHz, CDCl3) δ 29.5, 32.1, 50.4, 129.3, 131.1, 134.5, 147.4, 192.2 MS(EI):m / z (%) 57(50), 91(45), 120(100), 161(10), 176(M +· , 5)

[0059] [ka]

[0060] <Synthesis of 4-neopentyltoluene> 50.0g (0.28mol) of 4-neopentylbenzaldehyde, 25.0g of heptane, and 2.5g (5wt%) of 10% Pd / C were added to a 200mL autoclave, and the inside of the reactor was replaced with nitrogen and then with hydrogen. The pressure was increased to 1.0MPaG with hydrogen, and the temperature was raised to 50℃ while stirring. After the temperature was raised, the reaction was carried out for 10 hours while maintaining the temperature at 1.0MPaG and 50℃. The resulting crude reaction solution was filtered to remove the catalyst, and the filtrate was concentrated using a rotary evaporator. The resulting concentrate was purified by distillation (97° C., 20 Torr) to obtain 33.9 g (0.21 mol) of 4-neopentyltoluene as a colorless, transparent liquid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained 4-neopentyltoluene are as follows:

[0061] [4-Neopentyltoluene] 1 H NMR (400 MHz, CDCl3) δ 0.89 (9H, s), 2.31 (3H, s), 2.45 (2H, s), 6.99-7.02 (2H, d, J = 8.4Hz), 7.05-7.07 (2H, d, J = 8.4Hz) 13 C NMR (100 MHz, CDCl3) δ 21.2, 29.5, 31.8, 50.0, 128.5, 130.5, 135.2, 136.8 MS(EI):m / z (%) 57(88), 77(12), 91(41), 106(100), 147(17), 162(M +· , 48)

[0062] [ka]

[0063] <Synthesis of 3-neopentyltoluene> A 500 mL autoclave equipped with a nack-drive stirrer, three inlet nozzles at the top and one outlet nozzle at the bottom, and with an internal temperature controllable by a jacket, was used as the isomerization reactor. A coolant was passed through the jacket of the autoclave and cooled to 0° C., and 191.5 g (9.57 mol) of hydrogen fluoride was charged into the autoclave. Thereafter, while stirring and adjusting the temperature so that it did not exceed 15°C, 47.7 g (0.70 mol) of boron trifluoride was added. After the addition of boron trifluoride, a mixed solution of 38.5 g (0.24 mol) of 4-neopentyltoluene and 38.5 g of hexane was added while maintaining the temperature inside the autoclave at 15°C. After stirring for 4 hours while maintaining the temperature at 15°C, the reaction mixture in the autoclave was drained into ice water. After the drained liquid was thoroughly mixed, the oil layer was separated and neutralized by washing with water. This procedure was repeated three times, and the total oil layer was concentrated using a rotary evaporator. The concentrate was purified by distillation (93° C., 20 Torr) to obtain 87.0 g (0.53 mol) of 3-neopentyltoluene as a colorless, transparent liquid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained 3-neopentyltoluene are as follows.

[0064] [3-Neopentyltoluene] 1 H NMR (400 MHz, CDCl3) δ 0.90 (9H, s), 2.33 (3H, s), 2.45 (2H, s), 6.91-6.93(1H, d, J = 8.0Hz), 6.93 (1H, s), 7.00-7.02 (1H, d, J = 7.6Hz), 7.13-7.17 (1H, t, J = 7.6Hz) 13 C NMR (100 MHz, CDCl3) δ 21.6, 29.6, 31.8, 50.3, 126.6, 127.6, 127.7, 131.4,137.1, 139.8 MS(EI):m / z (%) 57(96), 77(13), 91(45), 106(100), 147(16), 162(M +· , 48)

[0065] [ka]

[0066] <Synthesis of 2-methyl-4-neopentylbenzaldehyde> A 500 mL autoclave equipped with a nack-drive stirrer, three inlet nozzles at the top and one outlet nozzle at the bottom, and with an internal temperature controllable by a jacket, was used as the formylation reactor. A coolant was passed through the jacket of the autoclave, which had been cooled to −25° C., and 43.0 g (2.15 mol) of hydrogen fluoride was charged into the autoclave. Thereafter, while stirring and adjusting the temperature so that it did not exceed -25°C, 29.5 g (0.44 mol) of boron trifluoride was added. After the boron trifluoride was added, the temperature inside the autoclave was kept at -25°C and the pressure was increased to 2 MPaG with carbon monoxide, and a mixed solution of 47.1 g (0.29 mol) of 3-neopentyltoluene and 47.1 g of heptane was added. After stirring for 120 minutes while maintaining the temperature at -25°C and the pressure at 2MPaG, the reaction mixture in the autoclave was drained into ice water. After shaking the drained liquid well, the oil layer was separated and the obtained oil layer was neutralized and washed with water. These operations were carried out twice, and the combined oil layer was concentrated using a rotary evaporator. The concentrate was then purified by distillation (139°C, 15 Torr) to obtain 82.1 g (0.43 mol) of 2-methyl-4-neopentylbenzaldehyde as a colorless, transparent liquid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained 2-methyl-4-neopentylbenzaldehyde are as follows.

[0067] [2-Methyl-4-neopentylbenzaldehyde] 1H NMR (400 MHz, CDCl3) δ 0.92 (9H, s), 2.52 (2H, s), 2.65 (3H, s), 7.01 (1H, s), 7.11-7.13 (1H, d, J = 7.6Hz), 7.69-7.71 (1H, d, J = 7.6Hz), 10.23 (1H, s) 13 C NMR (100 MHz, CDCl3) δ 19.7, 29.5, 32.1, 50.3, 128.5, 131.8, 132.3, 133.9, 139.9, 146.4, 192.5 MS(EI):m / z (%) 57(65), 77(8), 91(26), 105(40), 134(100), 175(11), 190(M +· , 29)

[0068] [ka]

[0069] <Synthesis of (E)-3-(2-methyl-4-neopentylphenyl)propenal> Into a 100 mL round-bottom flask were placed 15.0 g (0.08 mol) of 2-methyl-4-neopentylbenzaldehyde, 15 g of methanol as a solvent, and 2.1 g (0.03 mol) of a 50% aqueous NaOH solution as a catalyst, and the mixture was cooled to 10°C. Thereafter, 3.9 g (0.09 mol) of acetaldehyde was added dropwise while stirring and adjusting the temperature so as not to exceed 15° C. After reacting for 2 hours, the mixture was quenched by adding 2.0 g (0.03 mol) of acetic acid. After quenching, extraction and separation were performed using heptane, the resulting oil layer was dried over magnesium sulfate, and the filtrate obtained by filtration was concentrated using a rotary evaporator. The obtained concentrate was purified by column chromatography (silica gel, hexane:ethyl acetate=93:7) to obtain 5.0 g (0.02 mol) of (E)-3-(2-methyl-4-neopentylphenyl)propenal as a yellow solid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained (E)-3-(2-methyl-4-neopentylphenyl)propenal are as follows.

[0070] [(E)-3-(2-methyl-4-neopentylphenyl)propenal] 1 H NMR (400 MHz, CDCl3) δ 0.92 (9H, s), 2.47 (3H, s), 2.49 (2H, s), 6.63-6.69(1H, dd, J = 7.6Hz, 16Hz), 7.01 (1H, s), 7.01-7.03 (1H, d, J = 9.6Hz), 7.51-7.53 (1H, d, J = 7.6Hz), 7.74-7.78 (1H, d, J = 16Hz), 9.70-9.72 (1H, d, J = 7.6Hz) 13 C NMR (100 MHz, CDCl3) δ 19.9, 29.6, 32.1, 50.2, 126.3, 128.8, 129.0, 130.5, 133.3, 137.4, 143.7, 150.6, 194.1 MS(EI):m / z (%) 57(71), 91(11), 115(16), 131(17), 145(100), 160(70), 201(29), 216(M +· , 16)

[0071] [ka]

[0072] <Synthesis of 3-(2-methyl-4-neopentylphenyl)propanal> 0.7g (0.003 mol) of (E)-3-(2-methyl-4-neopentylphenyl)propenal, 35.0g of heptane as a solvent, and 0.07g (10wt%) of 10% Pd / C as a catalyst were added to a 200mL autoclave, and the inside of the reactor was replaced with nitrogen and then with hydrogen. The pressure was then increased to 0.1MPaG with hydrogen and stirred. After the pressure increase, the mixture was kept at 0.1MPaG and 25°C and reacted for 1 hour. The resulting crude reaction solution was filtered to remove the catalyst, and the filtrate was concentrated using a rotary evaporator. The resulting concentrate was purified using column chromatography (silica gel, hexane:ethyl acetate=96:4) to obtain 0.4 g (0.002 mol) of 3-(2-methyl-4-neopentylphenyl)propanal as a colorless, transparent liquid. The structural formula, NMR spectrum, mass spectrometry and fragrance note of the obtained 3-(2-methyl-4-neopentylphenyl)propanal are as follows:

[0073] [3-(2-methyl-4-neopentylphenyl)propanal] 1 H NMR (400 MHz, CDCl3) δ 0.89 (9H, s), 2.29 (3H, s), 2.42 (2H, s), 2.71-2.75 (2H, t, J = 7.8Hz), 2.90-2.94 (2H, t, J = 7.8Hz), 6.89-6.91 (1H, d, J = 7.6Hz),6.91 (1H, s), 7.00-7.02 (1H, d, J = 7.2Hz), 9.85 (1H, s) 13 C NMR (100 MHz, CDCl3) δ 19.5, 25.2, 29.5, 31.8, 44.2, 49.8, 127.8, 128.4, 132.7, 135.1, 135.7, 138.0, 202.0 MS(EI):m / z (%) 57(100), 77(7), 91(19), 105(19), 118(57), 129(28), 144(90), 162(25), 203(8), 218(M +· , 30) Fragrance: Lily of the valley, white floral, aldehyde, green The fragrance had a slightly stronger marine, fatty note than Lilial, and was somewhere between Lilial and Silvial.

[0074] [ka]

[0075] <Synthesis of (E)-3-(2-methyl-4-neopentylphenyl)-2-methylpropenal> Into a 100 mL round-bottom flask were placed 15.0 g (0.08 mol) of 2-methyl-4-neopentylbenzaldehyde, 15.0 g of methanol as a solvent, and 2.0 g (0.03 mol) of a 50% aqueous NaOH solution as a catalyst, and the mixture was kept at 25°C. Thereafter, 5.0 g (0.09 mol) of propionaldehyde was added dropwise while stirring and adjusting the temperature so as not to exceed 25° C. After reacting for 2 hours, the mixture was quenched by adding 1.6 g (0.03 mol) of acetic acid. After quenching, extraction and separation were performed using heptane, the resulting oil layer was dried over magnesium sulfate, and the filtrate obtained by filtration was concentrated using a rotary evaporator. The obtained concentrate was purified by column chromatography (silica gel, hexane:ethyl acetate=95:5) to obtain 13.3 g (0.06 mol) of (E)-3-(2-methyl-4-neopentylphenyl)-2-methylpropenal as a yellow liquid. The structural formula, NMR spectrum, and mass spectrometry results of the obtained (E)-3-(2-methyl-4-neopentylphenyl)-2-methylpropenal are as follows.

[0076] [(E)-3-(2-methyl-4-neopentylphenyl)-2-methylpropenal] 1H NMR (400 MHz, CDCl3) δ 0.93 (9H, s), 1.98 (3H, s), 2.35 (3H, s), 2.49 (2H, s), 7.01-7.03 (1H, d, J = 6.4Hz), 7.03 (1H, s), 7.28-7.30 (1H, d, J = 8.4Hz), 7.43 (1H, s), 9.63 (1H, s) 13 C NMR (100 MHz, CDCl3) δ 11.0, 19.9, 29.4, 31.8, 50.0, 127.9, 128.3, 131.4, 132.6, 136.5, 138.5, 141.3, 148.3, 195.5 MS(EI):m / z (%) 57(56), 91(7), 105(7), 115(10), 128(12), 145(11), 159(100), 174(33), 215(46), 230(M +· ,12)

[0077] [ka]

[0078] <Synthesis of 3-(2-methyl-4-neopentylphenyl)-2-methylpropanal> (E)-3-(2-methyl-4-neopentylphenyl)-2-methylpropenal 13.3g (0.06 mol), 5wt% Na2CO3 aqueous solution 40.0g, and 5% Pd / C 0.3g (2wt%) were added to a 200mL autoclave, and the inside of the reactor was replaced with nitrogen and then with hydrogen. The pressure was then increased to 0.4MPaG with hydrogen, and the temperature was increased to 75°C while stirring. After the temperature increase, the temperature was kept at 0.4MPaG and 75°C, and the reaction was carried out for 7 hours. The resulting crude reaction solution was filtered to remove the catalyst, and the filtrate was concentrated using a rotary evaporator. The resulting concentrate was purified by column chromatography (silica gel, hexane:ethyl acetate=96:4), and then distilled (102°C, 1 Torr) to obtain 6.7g (0.03 mol) of 3-(2-methyl-4-neopentylphenyl)-2-methylpropanal as a colorless, transparent liquid. The structural formula, NMR spectrum, mass spectrometry and fragrance notes of the obtained 3-(2-methyl-4-neopentylphenyl)-2-methylpropanal are as follows:

[0079] [3-(2-methyl-4-neopentylphenyl)-2-methylpropanal] 1 H NMR (400 MHz, CDCl3) δ 0.89 (9H, s), 1.10-1.12 (3H, d, J = 6.8Hz), 2.29 (3H, s), 2.43 (2H, s), 2.54-2.57 (1H, dd, J = 8.4Hz, 14.0Hz), 2.63-2.68 (1H, m), 3.05-3.10 (1H, dd, J = 6.0Hz, 14.0Hz), 6.89-6.91 (1H, d, J = 7.6Hz), 6.92 (1H, s), 6.99-7.01 (1H, d, J = 7.6Hz), 9.72 (1H, s) 13 C NMR (100 MHz, CDCl3) δ 13.6, 19.6, 29.5, 31.8, 33.7, 47.0, 49.8, 128.2, 129.0, 032.8, 134.4, 135.3, 138.0, 204.7 MS(EI):m / z (%) 57(93), 77(6), 91(12), 105(27), 119(100), 131(8), 143(24), 158(64), 175(25), 214(8), 232(M +· ,38) Fragrance: Lily of the valley, white floral, green, woody The fragrance is not as marine-like and fatty as Lilial, and has a weak aldehyde scent, but is more woody-amber-like and has a beautiful muget note. Fragrance-wise, I felt that it had great potential.

[0080] [ka]

[0081] <Compositional Fragrance Evaluation-1> From the results of the fragrance evaluation, it was revealed that 3-(2-methyl-4-neopentylphenyl)propanal has a fragrance similar to Lilial and Silvial. Therefore, 3-(2-methyl-4-neopentylphenyl)propanal was added instead of Lilial to the following three model formulations of Lilial and evaluated. Formulations 1 to 3 are shown in the table below. Formulation 1 has a floral powdery fragrance, Formulation 2 has a Muguet fragrance, and Formulation 3 has a fruity floral fragrance.

[0082] [Table 1-1]

[0083] [Table 1-2]

[0084] [Table 1-3]

[0085] [Formulation 1: Examples 1-1 and 1-2] In Example 1-1, a blended fragrance was prepared in the same manner as in Formulation 1, except that 320 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal was added instead of 320 parts by mass of Lilial, and its fragrance tone was evaluated. In Example 1-2, a blended fragrance was prepared and its fragrance was evaluated in the same manner, except that 120 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal and 200 parts by mass of dipropylene glycol were added instead of 320 parts by mass of lilial in Formulation 1. That is, in Example 1-2, the amount of lilial added was reduced to 37.5% and the evaluation was performed. Dipropylene glycol is odorless and is added to dilute the 3-(2-methyl-4-neopentylphenyl)propanal.

[0086] [Formulation 2: Examples 2-1 and 2-2] In Example 2-1, a blended fragrance was prepared in the same manner as in Formulation 2, except that 350 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal was added instead of 350 parts by mass of Lilial, and its fragrance tone was evaluated. In Example 2-2, a blended fragrance was prepared in the same manner as above, except that 150 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal and 200 parts by mass of dipropylene glycol were added instead of 350 parts by mass of lilial in Formulation 2, and the fragrance tone was evaluated. That is, in Example 2-2, the amount of lilial added was reduced to 42.9% and the evaluation was performed.

[0087] [Formulation 3: Examples 3-1 and 3-2] In Example 3-1, a blended fragrance was prepared in the same manner as in Formulation 3, except that 50 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal was added instead of 50 parts by mass of Lilial, and its fragrance tone was evaluated. In Example 3-2, a blended fragrance was prepared and its fragrance was evaluated in the same manner, except that 20 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal and 30 parts by mass of dipropylene glycol were added instead of 50 parts by mass of Lilial in Formulation 3. That is, in Example 3-2, the amount of Lilial added was reduced to 40% and the evaluation was performed.

[0088] [Fragrance Evaluation] The evaluation of the fragrance notes of the blended fragrances was carried out by diluting the above formulations 1 to 3 ten-fold with 9,000 parts of triethyl citrate. The samples were soaked into filter paper measuring 8 mm in width and 15 cm in length, and evaluated by a panel of experts who smelled them.

[0089] As a result of evaluating the fragrance of the blended fragrances, the blended fragrances prepared in Examples 1-1, 2-1, and 3-1 were compared with Formulations 1 to 3, respectively, and it was found that the fragrances were similar to those of Formulations 1 to 3, which are blended fragrances containing added lilial, but the fragrance was stronger. In addition, when the fragrance tone was evaluated in Examples 1-2, 2-2, and 3-2, in which the amount of addition was reduced, the fragrance was perceived to be as strong as when lilial was added, indicating that 3-(2-methyl-4-neopentylphenyl)propanal is a fragrance with greater potency than lilial.

[0090] <Evaluation of lingering fragrance> The lingering fragrance was evaluated by comparing it with Lilial. 3-(2-methyl-4-neopentylphenyl)propanal and Lilial were each impregnated into a portion of the tip of approximately 1 cm of filter paper measuring 8 mm in width and 15 cm in length, and the fragrance strength was evaluated immediately after impregnation. The filter paper was then left at room temperature, and the fragrance strength was evaluated after 6 hours and 18 hours.

[0091] As a result of evaluating the lingering fragrance, 3-(2-methyl-4-neopentylphenyl)propanal had a strong fragrance even after 6 hours, and was perceived to be stronger than Lilial. After 18 hours, 3-(2-methyl-4-neopentylphenyl)propanal still had a fragrance, whereas Lilial was barely perceptible.

[0092] <Compositional Fragrance Evaluation-2> JP 2018-138550 A describes the following compound (hereinafter, Nympheal) as an alternative fragrance to Lilial. Therefore, 3-(2-methyl-4-neopentylphenyl)propanal was added instead of Nympheal to the following two model formulations of Nympheal, and an evaluation was performed. Formulations 4 and 5 are shown in the table below. Formulation 4 has a green floral fragrance, and Formulation 5 has a floral fruity fragrance.

[0093] [ka]

[0094] [Table 2-1]

[0095] [Table 2-2]

[0096] Formulation 4: Example 4 In Example 4, a blended fragrance was prepared in the same manner as in Formulation 4, except that 50 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal was added instead of 50 parts by mass of Nympheal, and its fragrance tone was evaluated.

[0097] Formulation 5: Example 5 In Example 5, a blended fragrance was prepared in the same manner as in Formulation 5, except that 180 parts by mass of 3-(2-methyl-4-neopentylphenyl)propanal was added instead of 180 parts by mass of Nympheal, and its fragrance tone was evaluated.

[0098] [Fragrance Evaluation] The evaluation of the fragrance notes of the blended fragrances was carried out using the above formulations 4 and 5. The samples were soaked into filter paper measuring 8 mm in width and 15 cm in length, and evaluated by a panel of experts who smelled them.

[0099] As a result of evaluating the fragrance notes of the blended fragrances, the blended fragrances prepared in Examples 4 and 5 were compared with Formulations 4 and 5, respectively, and it was found that Examples 4 and 5 were superior in terms of the impact and strength of the middle note. More specifically, a solid and powerful green-floral feeling was more strongly observed about 30 minutes to 3 hours later. [Industrial Applicability]

[0100] The compound represented by formula (1) of the present invention is useful as a fragrance (a blended fragrance raw material), and is expected to be used as an alternative fragrance to lilial. Furthermore, it has been revealed that the compound represented by formula (1) of the present invention is a fragrance superior in potency and fragrance retention compared to lilial. It has also been revealed that the compound is an excellent fragrance, especially superior in the strength of the middle note, compared to Nympheal, another alternative fragrance to lilial.

Claims

1. A compound represented by the following formula (1): 【Chemistry 1】 (In formula (1), R is a hydrogen atom.)

2. A fragrance composition comprising the compound according to claim 1.

3. 2. Use of the compound according to claim 1 as a fragrance.

4. A step of subjecting the compound represented by formula (2) to aldol condensation with acetaldehyde to obtain a compound represented by formula (3); and a step of hydrogenating a compound represented by formula (3) to obtain a compound represented by formula (1). 【Chemistry 2】 【Chemistry 3】 (In formula (3), R is a hydrogen atom.) 【Chemistry 4】 (In formula (1), R is a hydrogen atom.)

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