Process for preparing phenyl propanal derivatives

Abstract

The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I). More particularly, it concerns valuable new chemical intermediates for producing perfuming ingredients. Moreover, the present invention also comprises a process for producing compounds of formula (I).

Description

[0001] PROCESS FOR PREPARING PHENYL PROP ANAL DERIVATIVES

[0002] Technical field

[0003] The present invention relates to the field of perfumery. More particularly, it concerns valuable new chemical intermediates for producing perfuming ingredients. Moreover, the present invention also comprises a process for producing compounds of formula (I).

[0004] Background of the invention

[0005] In the perfumery industry, there is a constant need to provide compounds imparting novel organoleptic notes. In particular, there is an interest towards ingredients imparting the lily of the valley odor or at least one of the key organoleptic facets of the lily of the valley odor. So, compounds imparting said note are particularly sought after to reconstitute the delicate floral odor of muguet which does not survive even the mildest of extraction methods to yield an essential oil. Towards this goal, compounds of formula (I), such as 1H- Indene-ar-propanal, 2, 3 -dihydro- 1,1 -dimethyl also known as Hivernal® (origin: Firmenich SA), 3-(4-isopropyl-2-methylphenyl)propanal, 3-(4-isopropylphenyl)-2-methylpropanal, 3-(4-(tert-butyl)phenyl)-2-methylpropanal; were previously reported in various prior arts as ingredients imparting Muguet note. The compounds of formula (I) may be prepared by various route such as hydroformylation, palladium-catalyzed coupling; Muller-Cunradi- Pieroh followed by hydrogenation. However, the reported route to obtain compounds of formula (I) suffers from the use of costly precious metal such as rhodium, palladium or ruthenium and from the generation of a complex mixture of isomers. In addition, being products of industrial interest, there is always a need for new processes showing improved yields and increased conversions.

[0006] So, there is a need to develop an approach toward compounds of formula (I) more sustainable allowing avoiding the generation of waste and using abundant and less expensive reagents while limiting the formation of isomers and using starting material easily available.

[0007] The present invention is a process for obtaining compound of formula (I) starting from compound of formula (II) due to a novel route through novel intermediate, never disclosed before, while controlling the isomers formed. In particular, most of the compounds of formula (II) which are an object of the present invention, have never been reported or suggested in the context of the preparation of compounds of formula (I).

[0008] Description of the invention

[0009] It has now been surprisingly found that compound of formula (I) may be obtained from compound of formula (II) allowing to reduce the number of steps and the cost of the preparation while avoiding the presence of other isomers. The invention’s process opens a new route allowing obtaining compound of formula (I) in less steps with overall higher yield, compared to the methods known from the prior arts.

[0010] So, the first object of the invention is a process for the preparation of a compound of formula (I) in the form of any one of its isomers or a mixture thereof; wherein

[0011] R and R1, independently from each other, represent a hydrogen atom or a Ci- 6 alkoxyl group or a Ci-6 alkyl group optionally substituted by one or two of a hydroxy, Ci-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a Ci-3 alkyl group; and provided that at least one group among R and R1is not a hydrogen atom ;

[0012] R2represents a hydrogen atom or a methyl group; and

[0013] R’ is an hydrogen atom; or

[0014] R and R’ are taken together and represent a C3-8 alkanediyl or a -0-(CH2)m- O- wherein m is 1 or 2; comprising the oxidative cleavage of compound of formula (II) in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R3, R and R’ have the same meaning as defined above; Raand Rb, independently from each other, are a hydrogen atom or a Ci-16 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above.

[0015] For the sake of clarity, by the expression “any one of its stereoisomers or a mixture thereof’, or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the compound of formula (I) and (II) can be a pure enantiomer or diastereomer. In other words, the compound of formula (I) and (II) may possess several stereocenters and each of said stereocenter can have two different stereochemistries (e.g. R or S). The compound of formula (I) and (II) may even be in the form of a pure enantiomer or in the form of a mixture of enantiomers or diastereoisomers. The compound of formula (I) and (II) can be in a racemic form or scalemic form. Therefore, the compound of formula (I) and (II) can be one stereoisomers or in the form of a composition of matter comprising, or consisting of, various stereoisomers.

[0016] According to any one of the above embodiments of the invention, the compound of formula (II) can be in the form of its E or Z isomer or of a mixture thereof, e.g. the invention comprises compositions of matter consisting of one or more compounds of formula (II), having the same chemical structure but differing by the configuration of the double bond. In particular, compound (II) can be in the form of a mixture consisting of isomers E and Z and wherein said isomers E represent at least 50 % of the total mixture, or even at least 75% (i.e a mixture E / Z comprised between 75 / 25 and 100 / 0).

[0017] The terms “alkyl”, “alkoxyl” and “alkanediyl” are understood as comprising branched and linear alkyl and alkanediyl groups.

[0018] It is understood that by “... hydrocarbon group ...” it is meant that said group consists of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), a linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g. cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e. aryl group, or can also be in the form of a mixture of said type of groups, e.g. a specific group may comprise a linear alkyl, a branched alkenyl (e.g. having one or more carbon-carbon double bonds), a (poly)cycloalkyl and an aryl moiety, unless a specific limitation to only one type is mentioned. Similarly, in all the embodiments of the invention, when a group is mentioned as being in the form of more than one type of topology (e.g. linear, cyclic or branched) and / or being saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is also meant a group which may comprise moieties having any one of said topologies or being saturated or unsaturated, as explained above. Similarly, in all the embodiments of the invention, when a group is mentioned as being in the form of one type of saturation or unsaturation, (e.g. alkyl), it is meant that said group can be in any type of topology (e.g. linear, cyclic or branched) or having several moieties with various topologies. It is preferred that the hydrocarbon group does not have any C-C-double bonds.

[0019] As a consequence, the term " any one of its isomers or a mixture thereof used for compound of the formula (I) is used in the sense of "any one of its stereoisomers or a mixture thereof, as described above.

[0020] The term " any one of its isomers or a mixture thereof used for compound of the formula (II), however, is used in the sense of "any one of its stereoisomers or a mixture thereof, as described above, as well "in the form of its E or Z isomer or of a mixture thereof, as described above.

[0021] It is understood that with the term “. . . a hydrocarbon group, optionally comprising one or more oxygen atoms. . .” it is meant that said hydrocarbon group optionally comprises one, two, three or more oxygen atoms in a form of alcohol, ketone, aldehyde, ether, ester, carboxylic acid, carbonate groups. These groups can either substitute a hydrogen atom of the hydrocarbon group and thus be laterally attached to said hydrocarbon, or substitute a carbon atom (if chemically possible) of the hydrocarbon group and thus be inserted into the hydrocarbon chain. For example, a -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group comprising an alcohol group (substitution of a hydrogen atom), i.e. a C4 hydrocarbon comprising an oxygen atom; a -CH2-CH2-COO-CH2-CH2CH2-CH2- group represents a C7 hydrocarbon group comprising one ester group (substitution of carbon atoms / insertion into the hydrocarbon chain), i.e. a C7 hydrocarbon comprising two oxygen atoms and, similarly, a -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a Ce hydrocarbon group comprising two ether groups, i.e. a Ce hydrocarbon comprising two oxygen atoms. The term “optionally” is understood that a certain group to be optionally substituted can or cannot be substituted with a certain functional group.

[0022] By the term “oxidative cleavage” or similar, it is meant the normal meaning in the art; i.e. a reaction in which a carbon-carbon double bond is cleaved and oxidized generating two compounds having a carbon-oxygen double bond, such as aldehyde, ketone, acid, ester. Under certain conditions, the aldehyde or ketone formed may be converted in situ in the corresponding acetal.

[0023] According to any embodiments of the invention, R2is a hydrogen atom.

[0024] According to any embodiments of the invention, R and R’ are taken together and represent a C4-8 alkanediyl or a -0-(CH2)m-0- wherein m is 1 or 2. Particularly, R and R’ are taken together and represent a C4-6 alkanediyl or a -0-(CH2)m-0- wherein m is 1 or 2. Particularly, R and R’ are taken together and represent a C5-6 alkanediyl or a -0-(CH2)m-0- wherein m is 1 or 2. Even more particularly, R and R’ are taken together and represent a -C(CH3)2- (CH2)2- or a -O-(CH2)-O- group.

[0025] According to any embodiments of the invention, Ramay be a hydrogen atom or a Ci-14 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a C1-12 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-10 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula ) in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-8 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-6 hydrocarbon group, optionally comprising one to two oxygen atoms or a group of in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-6 hydrocarbon group, optionally comprising one to two oxygen atoms or a group of in the form of any one of its isomers or a mixture thereof; wherein R1and R have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-6 alkyl or a Ce aryl group or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1and R have the same meaning as defined above. Particularly; Ramay be a hydrogen atom or a Ci-6 alkyl or a Ce aryl group. Particularly; Ramay be a hydrogen atom or a Ci-6 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-4 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-3 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-2 alkyl group. Particularly; Ramay be a hydrogen atom or a methyl group. Particularly; Ramay be a hydrogen atom.

[0026] According to any embodiments of the invention, Rbmay be a hydrogen atom or a Ci-14 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a Ci-12 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a Ci-io hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a Ci-8 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a C1-6 hydrocarbon group, optionally comprising one to two oxygen atoms or a group of formula ) in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a

[0027] C1-6 hydrocarbon group, optionally comprising one to two oxygen atoms or a group of formula ') in the form of any one of its isomers or a mixture thereof; wherein R1and R have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a C1-6 alkyl or a Ce aryl group or a group of formula ') in the form of any one of its isomers or a mixture thereof; wherein R1and R have the same meaning as defined above. Particularly; Rbmay be a hydrogen atom or a Ci-6 alkyl or a Ce aryl group. Particularly; Rbmay be a hydrogen atom or a Ci-6 alkyl or a phenyl group. Particularly; Rbmay be a hydrogen atom or a C1-4 alkyl or a phenyl group. Particularly; Rbmay be a hydrogen atom or a C1-3 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-2 alkyl group. Particularly; Rbmay be a hydrogen atom or a methyl group. Particularly; Rbmay be a hydrogen atom.

[0028] It is particularly preferred that neither Ranor Rbcomprise any C-C double bond.

[0029] It is also preferred that none of the substituents R, R', R1, R2, Raand Rbcomprises any carbon-carbon double bond.

[0030] According to any embodiments of the invention, the compound of formula (I) is of formula (III) in the form of any one of its isomers or a mixture thereof; and wherein R and R1have the same meaning as defined above.

[0031] According to any embodiments of the invention, the compound of formula (II) is of formula (IV) in the form of any one of its isomers or a mixture thereof; and wherein R and R1have the same meaning as defined above.

[0032] According to any embodiments of the invention, R1may be a hydrogen atom or a Ci-6 alkoxyl group or a Ci-6 alkyl group optionally substituted by one or two of a hydroxy, a Ci-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a C1-3 alkyl group. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a C1-2 alkyl group. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a methyl group. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-4 alkoxyl or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-3 alkoxyl or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-2 alkoxyl or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-4 alkoxyl group or a C1-4 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-3 alkoxyl group or a C1-3 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H. Particularly, R1may be a hydrogen atom or a C1-2 alkoxyl group or a C1-2 alkyl group. Particularly, R1may be a hydrogen atom or a methyl or methoxy group. Particularly, R1may be a hydrogen atom or a methyl group. Even more particularly, R1may be a hydrogen atom.

[0033] According to any embodiments of the invention, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a C1-3 alkyl group. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a C1-2 alkyl group. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a methyl group. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-6 alkoxyl or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-4 alkoxyl or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-3 alkoxyl or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a C1-2 alkoxyl or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-6 alkoxyl group or a C1-6 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-4 alkoxyl group or a C1-4 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H. Particularly, R may be a hydrogen atom or a C1-3 alkoxyl group or a C1-4 alkyl group. Particularly, R may be a hydrogen atom or a C1-2 alkoxyl group or a C1-4 alkyl group. Particularly, R may be a hydrogen atom or a or methoxy or a C1-4 alkyl group. Particularly, R a C1-4 alkyl group. Even more particularly, R may be a propyl, a isoproly, a butyl, a isobutyl a tertbutyl group.

[0034] According to any embodiments of the invention, R is not a group of formula-CEh- C(Me)2OH. It is preferred that the compound of the formula (II) is a compound selected of the group consisting of the compounds of the formula (Ila), (lib), (lie), (lid) and (lie) particularly of formula (Ila) or (lie) or (lid), , p y 3.

[0035] According to any embodiments of the invention, the oxidative cleavage may be carried out under normal condition known by the person skilled in the art, i.e. in the presence of an oxidizing agent such as ozone, reaction also known as ozonolysis, OsCU / NaICU, KMnCU / NaICU, RuCh / NaICU, RuCh / NaOCl, EECh / NalCU or organic peroxide / NaIC Particularly, the oxidative cleavage may be an ozonolysis; i.e. compound of formula (II) reacts with ozone. Even more particularly, the oxidative cleavage may be an ozonolysis, followed by a reductive step.

[0036] It is to be stressed that due to high toxicity of pyridinium chlorochromate (PCC), PCC is excluded reagent used for the oxidative cleavage of this invention.

[0037] For the sake of clarity, by the expression “reductive steps” or similar it is understood by a person skilled in the art that the intermediate formed, to obtain compound of formula (I), is treated with at least one reducing agent, which is well known to a person skilled in the art. Such treatment with a reducing agent can be performed during the work-up. As nonlimiting examples of said reducing agents one may cite the following: an amine in particular a tertiary amine or a pyridine, a sulfite, such as an alkaline sulfite (e.g. sodium or potassium sulfite, sodium bisulfite) or a C2-6 dialkyl sulfide such as dimethyl sulfide or methylphenylsulfide, Na salt of 3,3 '-Thiodipropionic acid, triphenylphosphine, Zn / AcOH, Zn / AcOH / water, Na?S, thiourea, thiodiglycol, 3,3 '-thiodipropanol, 3,3 '-thiodipropionitrile, H2and Pd / C or Raney / Ni, P(OMe)3, P(OEt)3, P(OPh)3MeO(SO)OMe, MeSSMe, etc. In particular one may cite a sulfite, such as an alkaline sulfite (e.g. sodium or potassium sulfite, sodium bisulfite) optionally in combination with Na salt of 3,3 '-thiodipropionic acid or a C2-6 dialkyl sulfide such as dimethyl sulfide.

[0038] The ozonolysis can be carried out in the presence or absence of a solvent. When a solvent is required or used for practical reasons, then any solvent of current use in ozonolysis reactions can be used for the purposes of the invention. Non-limiting examples include water, C5-10 saturated hydrocarbon solvents such as hexane or cyclohexane, saturated C4-10 ethers or esters such as AcOEt, tetrahydrofuran, dioxane or MTBE, saturated carboxylic acids such as acetic or propionic acid, saturated polar solvents such as acetonitrile, alcohols such as isopropanol, methanol, butanol or ethanol, saturated ketones such as butanone or isobutylmethylketone, chlorinated alkane such as chloroform or dichloromethane, or mixtures thereof. The exact choice of the solvent is a function of the compound of formula (II) and reaction speed required. The person skilled in the art is well able to select the solvent most convenient in each case to optimize the ozonolysis reaction. Particularly, the solvent used in the ozonolysis comprise water; i.e. water only or at least one of organic solvent and water. Surfactants may also be added in the reaction medium, particularly when the solvent used in the ozonolysis comprise water. The water can be added to the reaction medium in a large range of concentrations. As non-limiting examples, one can cite as water concentration values ranging from 0.5 wt% to 5 wt%, relative to the amount of the compound of formula (II). Non-limiting examples of suitable surfactant may include sodium dodecyl sulfate, bis[4-({2-(methoxycarbonyl) phenyl }amino)-4- oxobutanoic acid]-polyethylene glycol 1000, Triton X-100, TPGS-750-M.

[0039] The temperature at which the oxidation can be carried out is preferably in the range of between -100°C and 40°C, particularly, in the range of between -80°C and 20°C, particularly, in the range of between -40°C and 10°C, particularly, in the range of between -20°C and 10°C, particularly, in the range of between -10°C and 10°C, even more particularly, in the range of between 0°C and 10°C. Of course, a person skilled in the art is able to select the preferred temperature as a function of the melting and boiling point of the starting and final products as well as the desired time of reaction or conversion.

[0040] The ozone can be added to the reaction medium in a large range of concentrations. As non-limiting examples, one can cite as ozone concentration values ranging from 0.5 wt% to 20 wt% in oxygen or air. It goes without saying that the optimum concentration of ozone will depend, as the person skilled in the art knows, on the nature of the compound of formula (II), if the process is run in batch or continuously, the desired conversion, as well as the desired time of reaction. Of course, a person skilled in the art is well able to adjust the pressure or the flow (e.g. in a continuous process) of the ozone to obtain this range of concentration as a function of the process is batch or continuous.

[0041] The reducing agent can be added to the reaction medium in a large range of concentrations. As non-limiting examples, one can cite as reducing agent concentration values those ranging from 0.5 molar equivalents to 10 molar equivalents, relative to the amount of compound of formula (II). Preferably, the reducing agent concentration will be comprised between 0.8 molar equivalents to 10 molar molar equivalents. Even more preferably, the reducing agent concentration will be comprised between 1.0 molar equivalents to 5 molar equivalents. It goes without saying that the optimum concentration of reducing agent will depend, as the person skilled in the art knows, on the nature of the latter, on the nature of the compound of formula (II), the desired conversion, as well as the desired time of reaction.

[0042] The invention’s process can be carried out under batch or continuous conditions. According to a particular embodiment of the invention, the process is a continuous one.

[0043] According to any embodiments of the inventions, the compound of formula (II) may be prepared by a Grignard reaction; i.e. the compound of formula (II) is prepared by reacting (Ra)(Rb)C=CH-CHR2-X with a compound of formula (V) wherein R, R’, R1and R2have the same meaning as defined above; Raand Rb, independently from each other, are a hydrogen atom or a Ci-i6 hydrocarbon group, optionally comprising one to three oxygen atoms;

[0044] Y is a halogen atom;

[0045] Z is MgY or a halogen atom with the proviso that if Z is MgY then X is a halogen atom; if Z is a halogen atom then X is MgY; to obtain a compound of formula (II).

[0046] According to any embodiments of the inventions, the process for preparing compound of formula (I) comprises preferably the steps of a) reacting (Ra)(Rb)C=CH-CHR2-X with a compound of formula (V) wherein R, R’, R1and R2have the same meaning as defined above; Raand Rb, independently from each other, are a hydrogen atom or a C1-16 hydrocarbon group, optionally comprising one to three oxygen atoms;

[0047] Y is a halogen atom; s MgY or a halogen atom th the proviso that if Z is MgY then X is a halogen atom; if Z is a halogen atom then X is MgY; ain a compound of formula (II) as defined above; and b) the oxidative cleavage of compound of formula (II) to obtain the compound of formula (I).

[0048] According to any embodiments of the invention, According to any embodiments of the invention, Ramay be a hydrogen atom or a C1-14 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Ramay be a hydrogen atom or a C1-12 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Ramay be a hydrogen atom or a C1-10 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Ramay be a hydrogen atom or a C1-8 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Ramay be a hydrogen atom or a C1-6 hydrocarbon group, optionally comprising one to two oxygen atoms. Particularly; Ramay be a hydrogen atom or a C1-6 alkyl or a Ce aryl group. Particularly; Ramay be a hydrogen atom or a C1-6 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-4 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-3 alkyl or a phenyl group. Particularly; Ramay be a hydrogen atom or a C1-2 alkyl group. Particularly; Ramay be a hydrogen atom or a methyl group. Particularly; Ramay be a hydrogen atom.

[0049] According to any embodiments of the invention, Rbmay be a hydrogen atom or a Ci-14 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Rbmay be a hydrogen atom or a C1-12 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Rbmay be a hydrogen atom or a C1-10 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Rbmay be a hydrogen atom or a C1-8 hydrocarbon group, optionally comprising one to three oxygen atoms. Particularly; Rbmay be a hydrogen atom or a C1-6 hydrocarbon group, optionally comprising one to two oxygen atoms. Particularly; Rbmay be a hydrogen atom or a C1-6 alkyl or a Ce aryl group. Particularly; Rbmay be a hydrogen atom or a C1-6 alkyl or a Ce aryl group. Particularly; Rbmay be a hydrogen atom or a C1-6 alkyl or a phenyl group. Particularly; Rbmay be a hydrogen atom or a C1-4 alkyl or a phenyl group. Particularly; Rbmay be a hydrogen atom or a C1-3 alkyl or a phenyl group. Particularly; Rbmay be a hydrogen atom or a C1-2 alkyl group. Particularly; Rbmay be a hydrogen atom or a methyl group. Particularly; Rbmay be a hydrogen atom.

[0050] According to a particular embodiment of the inventions, the process for preparing compound of formula (I) comprises the step of a) reacting CH2=CH-CHR2-X with a compound of formula wherein R, R’, R1and R2have the same meaning as above;

[0051] Y is a halogen atom;

[0052] Z is MgY or a halogen atom with the proviso that if Z is MgY then X is a halogen atom; or if Z is a halogen atom then X is MgY; to obtain a compound of formula wherein R, R’, R1and R2have the same meaning as defined above; and b) the oxidative cleavage of compound of formula (VI) as defined above to obtain the compound of formula (I).

[0053] According to any preferred embodiments of the invention; Z is MgCl and then X is a Cl atom or Z is Cl atom and then X is MgCl. Particularly, Z is Cl atom and then X is MgCl.

[0054] The (Ra)(Rb)C=CH-CHR2-X can be added to the reaction medium in a large range of concentrations. As non-limiting examples, one can cite as (Ra)(Rb)C=CH-CHR2-X concentration values ranging from 1 to 2 equivalents, relative to the amount of the compound of formula (V). Preferably, the Ra)(Rb)C=CH-CHR2-X concentration will be comprised between 1.1 to 1,5 equivalents, relative to the amount of the compound of formula (IV) It goes without saying that the optimum concentration of (Ra)(Rb)C=CH- CHR2-X will depend, as the person skilled in the art knows, on the nature of the compound of formula (V), the desired conversion, as well as the desired time of reaction.

[0055] The preparation of compound of formula (II) or (VI) can be carried out in the presence or absence of a solvent. When a solvent is required or used for practical reasons, then any solvent wherein the compound of formula (V) is soluble and which is of current use in this kind reactions can be used for the purposes of the invention. Non-limiting examples include C5-10 saturated hydrocarbon solvents such as hexane or cyclohexane, aromatic solvent such as toluene, saturated C4-10 ethers such as tetrahydrofuran, methyltetrahydrofuran, 4-methyltetrahydropyran, dioxane or MTBE, or mixture thereof. The exact choice of the solvent is a function of the compound of formula (II) or (VI) and reaction speed required. The person skilled in the art is well able to select the solvent most convenient in each case to optimize this reaction

[0056] The temperature at which the preparation of the compound of formula (II) or (VI) can be carried out is comprised between -100°C and 100°C, particularly, in the range of between -80°C and 100°C, particularly, in the range of between -40°C and 80°C, particularly, in the range of between -20°C and 80°C, particularly, in the range of between -10°C and 80°C, even more particularly, in the range of between 0°C and 80°C. Of course, a person skilled in the art is able to select the preferred temperature as a function of the melting and boiling point of the starting and final products as well as the desired time of reaction or conversion.

[0057] Another object of the invention is a compound of formula (I) obtained by the process as defined above.

[0058] The compound of formula (II) is, generally, novel compounds and present a number of advantages as explained above and shown in the Examples. Therefore, another object of the present invention is a compound of formula in the form of any one of its isomers or a mixture thereof; wherein

[0059] R and R1, independently from each other, represent a hydrogen atom or a Ci- 6 alkoxyl group or a Ci-6 alkyl group optionally substituted by one or two of a hydroxy, Ci-6 alkoxyl or a OCHOR3group wherein R3is a hydrogen atom or a Ci-3 alkyl group; and provided that at least one group among R and R1is not a hydrogen atom; provided that R1is not a hydrogen atom when R is a C3-4 alkyl group ;

[0060] R2represents a hydrogen atom or a methyl group;

[0061] R’ is an hydrogen atom; or

[0062] R and R’ are taken together and represent a C3-8 alkanediyl;

[0063] Raand Rb, independently from each other, are a hydrogen atom or a C1-16 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formula in the form of any one of its isomers or a mixture thereof; R1, R2, Rand R’ have the same meaning as defined above.

[0064] It is particularly preferred that neither Ranor Rbcomprise any C-C double bond.

[0065] It is also preferred that none of the substituents R, R', R1, R2, Raand Rbcomprises any carbon-carbon double bond. It is further preferred that R1not a methyl or methoxy group when R is H.

[0066] It is further preferred that R is not a methyl or an ethyl or a n-propyl or a C1-3 alkoxy group, when R1is H.

[0067] It is particularly preferred that the compound of the formula (II) is not a compound selected from the group consisting of

[0068]

[0069] It is preferred that the compound of the formula (II) is a compound selected of the group consisting of the compounds of the formula (Ila), (lib), (lie), and (lid) particularly of formula (Ila). It is particularly preferred that the compound of the formula (I) is a compound selected from the group consisting of the compounds of the formula (la), (lb), (Ic) and (Id), particularly of formula (la) or (Ic) or (Id).

[0070] Typical manners to execute the invention’s process are reported herein below in the examples. Examples

[0071] The invention will now be described in further detail by way of the following examples, wherein the abbreviations have the usual meaning in the art, the temperatures are indicated in degrees centigrade (°C). NMR spectra were acquired using either a Bruker Avance II Ultrashield 400 plus operating at 400 MHz, (XH) and 100 MHz (13C) or a Bruker Avance III 500 operating at 500 MHz (XH) and 125 MHz (13C) or a Bruker Avance III 600 cryoprobe operating at 600 MHz (XH) and 150 MHz (13C). Spectra were internally referenced relative to tetramethyl silane 0.0 ppm. 'H NMR signal shifts are expressed in 8 ppm, coupling constants (J) are expressed in Hz with the following multiplicities: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; b, broad (indicating unresolved couplings) and were interpreted using Bruker Topspin software.13C NMR data are expressed in chemical shift 8 ppm and hybridization from DEPT 90 and DEPT 135 experiments, C, quaternary; CH, methine; CH2, methylene; CH3, methyl.

[0072] Example 1

[0073] Preparation of compound of formula (I) according to the invention process a) Preparation of l-(4-(but-3-en-l-yl)phenyl)-2-methylpropan-2-ol: l-(3-buten-l-yl)-4-chlorobenzene:

[0074] In a 250 ml round bottomed flask was charged allylmagnesium chloride (52.3 g, 2M in tetrahydrofuran, 105 mmol). This solution was stirred at 25 °C. A solution of 4-chlorobenzyl chloride (15.4 g, 91 mmol) in tetrahydrofuran (30.4 g) was added over a period of 2 hours. Reaction mixture was then stirred further for 1 hour and toluene was added (30 g). Reaction mixture was quenched with acetic acid (31 g, 20% aqueous solution) at 15°C. After decantation, phases were separated. The organic phase was washed twice with water, 5% NaHCOs solution and evaporated down to yield crude l-(3-buten-l-yl)-4-chlorobenzene (15.7 g) which was purified by distillation (12.7 g, 84% yield).

[0075] 5 H (500 MHz; CDC13; Me4Si) in ppm : 7.26-7.21 (m, 2H), 7.13-7.08 (m, 2H), 5.87-5.76 (m, 1H), 5.05- 4.95 (m, 2H), 2.67 (t, 2H), 2.38-2.31 (m, 2H) ppm.

[0076] 5 C (125 MHz; CDC13; Me4Si) in ppm : 140.2 (C), 137.6 (CH), 131.5 (C), 129.8 (CH), 128.4 (CH), 115.3 (CH2), 35.3 (CH2), 34.7 (CH2). 1-(4-(3-buten-l-yl)phenyl)-2-methylpropan-2-ol:

[0077] In a 500 ml round bottomed flask were charged magnesium (2.97 g, 122 mmol) and tetrahydrofuran (10 g). Reaction mixture was stirred and heated at 60°C. l-(3-buten-l-yl)-4- chlorobenzene (20 g, 120 mmol) was added over a period of 2 hours and more THF (70 g) was also added over a period of 1 hour. Reaction mixture was then stirred 20 hours at 60°C. Reaction mixture was then cooled down to 15°C, copper (I) chloride (0.12 g, 1.2 mmol) was added and isobutylene oxide (8.65 g, 120 mmol) was introduced over a period of 1 hour. Reaction mixture was quenched with citric acid (57.6 g, 20% aqueous solution) at 15°C, in the presence of 60% H2O2 (0.14 g, 2.4 mmol). Toluene (80 g) was added and reaction mixture was stirred for 1 hour. After decantation, phases were separated. Organic phase was washed with 10% potassium citrate solution, 5% NaHCO3 solution and evaporated down to yield crude l-(4-(3-buten-l-yl)phenyl)-

[0078] 2-methylpropan-2-ol (22.6 g) which was purified by distillation with a small column (16.2 g, 66% yield).

[0079] 5 H (500 MHz; CDC13; Me4Si) in ppm : 7.16-7.10 (m, 4H), 5.90-5.82 (m, 1H), 5.07-4.96 (m, 2H), 2.73 (s, 2H), 2.69 (t, 2H), 2.40-2.33 (m, 2H) 1.49 (br, 1H), 1.22 (s, 6H) ppm.

[0080] 5 C (125 MHz; CDC13; Me4Si) in ppm : 140 (C), 138.1 (CH), 135.1 (C), 130.4 (CH), 128.3 (CH), 114.9 (CH2), 70.7 (C), 49.3 (CH2), 35.5 (CH2), 35.0 (CH2), 29.1 (CH3). b) Ozonolysis of l-(4-(but-3-en-l-yl)phenyl)-2-methylpropan-2-ol in a ace tonitrile / w citer mixture.

[0081] A 1.5L glass reactor equipped with a magnetic stirring bar was charged in air with l-(4-(but-3- en-l-yl)phenyl)-2-methylpropan-2-ol (20g, 96 mmol) followed by acetonitrile (800 g) and water (80 g). The reaction mixture was stirred and cooled to 1°C with an ice / water bath. Then a O3 / O2 mixture at 0.55wt% of ozone with a flow of 40 L / h was sparge into the reaction mixture for a period of 8h. GC analysis of an aliquot (MTBE / PPhfl showed a full conversion and formation of aldehyde 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal in 92% with formation of the acid 3- (4-(2 -hydroxy-2 -methylpropyl)phenyl)propanoic acid in 7%. The reaction mixture is then poured into a separation funnel, diluted with toluene (800 ml) and the aqueous phase separated (42.5 g, pH 3-4). The organic phase is then washed successively with a solution of Na2SOs 10% (2 x 250 ml and 3 x 125 ml) followed by water (2 x 250 ml). The organic phase is then dried over anh. Na2SO4, filtered. The peroxide index was measured (IP < 10) and then the reaction mixture was concentrated in vacuo to give the desired crude aldehyde (17.8 g, GC 99%, 84.6 mmol, 88% yield). Distillation under reduced pressure (bp: 96°C / 0.001 mbar) gave 3-(4-(2-hydroxy-2- methylpropyl) phenyl)propanal (14.4 g, GC 99%, 69 mmol, 72% yield) as a colorless oil. 5H (500 MHz; CD2C12; Me4Si) in ppm: 1.17 (6H, s, Me), 1.43 (1H, br s, OH), 2.70 (2H, s), 2.75 (2H, t, J = 7.4 Hz, CH2), 2.92 (2H, t, J = 7.5 Hz, CH2), 7.13 (4H, s, CH arom.), 9.78 (1H, br s, CHO).

[0082] 5 C (125 MHz; CD2C12; Me4Si) in ppm : 28.06 (CH2), 29.39 (CH3), 45.63 (CH2), 49.61 (CH2), 70.89 (C), 128.36 (CH arom.), 131.03 (CH arom.), 136.35 (C arom.), 139.01 (C arom.), 201.98 (CHO).

[0083] Example 2 a) Preparation o / 2-methyl-l-(4-(4-methylpent-3-en-l-yl)phenyl)propan-2-ol

[0084] 1-chloro-4-(4-methylpent-3-en-l-yl)benzene

[0085] In a 2 L round bottomed flask were charged magnesium (15.1 g, 0.621 mol) and methyl tetrahydrofuran (400 g). This suspension was stirred at 20°C. A solution of 4-chlorobenzyl chloride (100 g, 0.621 mol) in methyl tetrahydrofuran (300 g) was added over a period of 2 hours. Reaction mixture was then stirred further for 1 hour. Prenyl chloride (74 g, 0.621 mol) was added over a period of 2 hours at 20°C. After 1 hour, reaction mixture was quenched with acetic acid (187 g, 20% aqueous solution) at 15°C. After decantation, phases were separated. Organic phase was washed twice with water, twice with 5% NaHCCh solution and evaporated down to yield crude l-chloro-4-(4-methylpent-3-en-l-yl)benzene (116.8 g) which was purified by distillation (88,3 g, 73% yield, containing also 8% of 1- chloro-4-(2,2-dimethylbut-3-en-l-yl)benzene). Desired main isomer was separated from minor isomer by fractionated distillation.

[0086] 'H NMR (500 MHz, CDC13): l-(3-buten-l-yl)-4-chlorobenzene; 5 = 7.25-7.22 (m, 2H), 7.12-7.08 (m, 2H), 5.15-5.10 (m, 1H), 2.59 (t, 2H), 2.29-2.23 (m, 2H), 1.68 (s, 3H) 1.54 (s, 3H) ppm.13C NMR (125 MHz, CDCI3): 5 = 140.8 (s), 132.5 (s), 131.4 (s), 129.8 (d), 128.3 (d), 123.2 (d), 35.4 (t), 29.9 (t), 25.7 (q), 17.7 (q) ppm.

[0087] 2-methyl-l-( 4-( 4-methylpent-3-en-l-yl)phenyl)propan-2-ol

[0088] In a 1 L round bottomed flask were charged magnesium (10.15 g, 0.418 mol) and methyl tetrahydrofuran (50 g). Reaction mixture was stirred and heated at 65°C. l-chloro-4-(4- methylpent-3-en-l-yl)benzene (80 g, 0.41 mol) was added over a period of 2 hours and more methyl tetrahydrofuran (270 g) was also added over a period of 1 hour. Reaction mixture was then stirred 44 hours at 65°C. Reaction mixture was then cooled down to 15°C, copper (I) chloride (0.41 g, 4.1 mmol) was added, and isobutylene oxide (29.5 g, 0.41 mol) was introduced over a period of 2 hours. Reaction mixture was quenched with citric acid (200 g, 20% aqueous solution) at 15°C, in the presence of 60% H2O2 (0.46 g, 8.2 mmol). Reaction mixture was stirred for 1 hour. After decantation, phases were separated. Organic phase was washed with 10% potassium citrate solution, 5% NaHCOs solution and evaporated down to yield crude 2-m ethyl- l-(4-(4-methylpent-3-en-l-yl)phenyl)propan-2- ol (108.6 g) which was purified by distillation with a small column (63.7 g, 67% yield).

[0089] 'H NMR (500 MHz, CDCI3): l-(4-(3-buten-l-yl)phenyl)-2-methylpropan-2-ol; 5 = 7.15- 7.10 (m, 4H), 5.20-5.15 (m, 1H), 2.73 (s, 2H), 2.63-2.58 (m, 2H), 2.25-2.31 (m, 2H) 1.68 (s, 3H), 1.56 (s, 3H), 1.22 (s, 6H) ppm.13C NMR (125 MHz, CDCI3): 5 = 140.6 (s), 134.9 (s), 132.1 (s), 130.3 (d), 128.3 (d), 123.8 (d), 70.7 (s), 49.3 (t), 35.7 (t), 30.1 (t), 29.1 (q), 5.7 (q), 17.7 (q) ppm. b) Ozonolysis of 2-methyl-l-(4-(4-methylpent-3-en-l-yl)phenyl)propan-2-ol

[0090] A 150mL glass reactor equipped with a magnetic stirring bar was charged in air with 2-methyl-

[0091] 1-(4-(4-methylpent-3-en-l-yl)phenyl)propan-2-ol (5g, 21 mmol) followed by di chloromethane (100 mL). The reaction mixture was stirred and cooled to -75°C. Then a O3 / O2 mixture at 2.5wt% of ozone with a flow of 30L / h was sparge into the reaction mixture for a period of Ih. GC analysis of an aliquot (MTBE / PPI13) showed a full conversion and formation of aldehyde 3-(4-(2-hydroxy-

[0092] 2-methylpropyl)phenyl)propanal. The reaction mixture is then quenched at -60°C with dimethylsulfide (3,lmL, 42mmol, 2eq) and stirred overnight. The aqueous layer is removed, and toluene is added (150 mL) to organic phase for extraction. The reaction mixture peroxide content was checked and then solvent was removed with rotavap to give 6.3g of crude material. Purification by bulb to bulb distillation gave the desired aldehyde 3-(4-(2-hydroxy-2- methylpropyl)phenyl)propanal (3g, 14.5mmol, 70% yield) as a slightly yellow colored oil.

[0093] 5H (500 MHz; CD2CI2; Me4Si) in ppm: 1.17 (6H, s, Me), 1.43 (IH, br s, OH), 2.70 (2H, s), 2.75 (2H, t, J = 7.4 Hz, CH2), 2.92 (2H, t, J = 7.5 Hz, CH2), 7.13 (4H, s, CH arom.), 9.78 (IH, br s, CHO). 5 C (125 MHz; CD2C12; Me4Si) in ppm : 28.06 (CH2), 29.39 (CH3), 45.63 (CH2), 49.61 (CH2), 70.89 (C), 128.36 (CH arom.), 131.03 (CH arom.), 136.35 (C arom.), 139.01 (C arom.), 201.98 (CHO).

[0094] Example 3

[0095] Ozonolysis of 5-(2-methylbut-3-enyl)-l,3-benzodioxole in Dichloromethane .

[0096] A 0.05L glass reactor equipped with a magnetic stirring bar was charged in air with 5-(2- methylbut-3-enyl)-l,3-benzodioxole (1.4 g, 7.4 mmol) followed by dichloromethane (26.5 g). The reaction mixture was stirred and cooled to -75°C with a dry ice / acetone bath. Then a Os / O2mixture at lwt% of ozone with a flow of 40 L / h was sparge into the reaction mixture for a period of Ih. GC analysis of an aliquot (MTBE / PPF13) showed a full conversion and formation of aldehyde 3-(l,3-benzodioxol-5-yl)-2-methyl-propanal in 90%. Triphenylphosphine (3.9g, 14.7 mmol) was added to the cold solution. The reaction mixture was slowly warmed-up to room temperature over Ih. then poured into a separation funnel, diluted with toluene (800 ml) and the aqueous phase separated (42.5 g, pH 3-4). The organic phase is then washed successively with a solution of Na2SOs 10% (2 x 250 ml and 3 x 125 ml) followed by water (2 x 250 ml). The organic phase is then dried over anh. Na2SO4, filtered. The peroxide index was measured (IP < 10) and then the reaction mixture was concentrated in vacuo to give the desired crude aldehyde (17.8 g, GC 99%, 84.6 mmol, 88% yield). Distillation under reduced pressure (bp: 96°C / 0.001 mbar) gave 3-(l,3-benzodioxol-5-yl)-2-methyl-propanal (0.57 g, GC 98%, 3 mmol, 40% yield) as a colorless oil.

[0097] 5 'H (500 MHz; CDCh; Me4Si) in ppm: 9.69 (d, IH, EAl.S Hz), 6.78-6.58 (m, 3H), 5.93 (s, 2H), 2.99 (dd, IH, J=5.4, 13.2 Hz), 2.57 (m, 2H), 1.08 (d, 3H, J=6.9 Hz).

[0098] 513C (125 MHz; CDCh; Me4Si) in ppm: 204.3, 147.7, 146.1, 132.5, 121.9, 109.3, 108.2, 100.9, 48.2, 36.4, 13.2.

[0099] Example 4

[0100] Ozonolysis of lH-Indene-ar-(but-3-en-yl)-2,3-dihydro-l , 1-dimethyl in Dichloromethane .

[0101] A 0.15L glass reactor equipped with a magnetic stirring bar was charged in air with IH-Indene- ar-(but-3 -en-yl)-2, 3 -dihydro-1, 1-dimethyl (5.0 g, 24.96 mmol) followed by dichloromethane (132.5 g). The reaction mixture was stirred and cooled to -75°C with a dry ice / acetone bath. Then a O3 / O2 mixture at 2wt% of ozone with a flow of 30 L / h was sparge into the reaction mixture for a period of Ih. GC analysis of an aliquot (MTBE / PPI13) showed a full conversion and formation of aldehyde IH-Indene-ar-propanal, 2, 3 -dihydro- 1,1 -dimethyl in 90%. Dimethylsulfide (4.8 g, 76.89 mmol) was added to the cold solution. The reaction mixture was slowly warmed-up to room temperature and stirred at room temperature for 17h. The peroxide index was measured (IP

[0102] < 10). The crude reaction mixture was purified by silica gel chromatography to give IH-Indene- ar-propanal, 2, 3 -dihydro- 1,1 -dimethyl (4.4 g, GC 90%, 21.75 mmol, 44% yield) as a colorless oil.

[0103] 5 'H (500 MHz, CDCI3; Me4Si) in ppm: 9.82-9.80 (m, IH), 7.12-6.94 (m, 3H), 2.93 (q, J 7.8, 2H), 2.87-20 2.82 (m, 2H9, 2.78-2.73 (m, 2H), 1.91 (t, J 7.2, 2H), 1.24 (s, 3H), 1.23

[0104] (s,3H).

[0105] 513C (125 MHz; CD2CI2; Me4Si) in ppm: 201.9, 201.9 (d), 153.1, 150.7 (s), 143.3, 140.9 (s), 138.4, 138.2 (s), 126.4, 126.2 (d), 124.5, 124.4 (d), 122.0, 121.9 (d), 45.7, 45.5 (t), 43.9, 43.6 (s), 41.6, 41.5 (t), 29.9, 29.6 (t), 28.6, 28.5 (q), 28.6 (q), 28.2, 28.0 (t).

Claims

Claims1. A process for the preparation of a compound of formula (I)in the form of any one of its isomers or a mixture thereof; whereinR and R1, independently from each other, represent a hydrogen atom or a Ci- 6 alkoxyl group or a Ci-6 alkyl group optionally substituted by one or two of a hydroxy, Ci-6 alkoxyl or a OC(O)R3group wherein R3is a hydrogen atom or a Ci-3 alkyl group; and provided that at least one group among R and R1is not a hydrogen atom ;R2represents a hydrogen atom or a methyl group; andR’ is an hydrogen atom; orR and R’ are taken together and represent a C3-8 alkanediyl or a -0-(CH2)m- O- wherein m is 1 or 2; comprising the oxidative cleavage of compound of formula (II)in the form of any one of its isomers or a mixture thereof; wherein R1, R2, R3, R and R’ have the same meaning as defined above; Raand Rb, independently from each other, are a hydrogen atom or a C1-16 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formulain the form of any one of its isomers or a mixture thereof; wherein R1, R2, R and R’ have the same meaning as defined above.

2. The process according to claim 1, wherein R2is hydrogen atom.

3. The process according to any one of claims 1 to 2, wherein Rais a hydrogen atom or a Ci-6 alkyl or a Ce aryl group; preferably Rais a hydrogen atom.

4. The process according to any one of claims 1 to 3, wherein Rbis a hydrogen atom or a Ci-6 alkyl, a Ce aryl group; preferably Rbis a hydrogen atom.

5. The process according to any one of claims 1 to 4, wherein the oxidative cleavage is an ozonolysis.

6. The process according to claim 5, wherein the ozonolysis is followed by a reductive step.

7. The process according to claim 6, wherein the reductive step is carried out with a reducing agent being selected from the group consisting of an amine in particular a tertiary amine or a pyridine, supported amine, a sulfite, a sulfide, Na salt of 3,3'- thiodipropionic acid, triphenylphosphine, Zn / AcOH, Zn / AcOH / water, Na?S, thiourea, thiodiglycol, 3,3 '-thiodipropanol, thioethanediol, 3,3 '-thiodipropionitrile, H2 and Pd / C or Raney / Ni, P(OMe)3, P(OEt)3, P(Oct)3, P(Ph)3P(OPh)3MeO(SO)OMe, MeSSMe.

8. The process according to any one of claims 1 to 7, wherein the ozonolysis is carried out in presence of water.

9. The process according to any one of claims 1 to 8, wherein the compound of formula (I) is of formulawherein R and R1have the same meaning as defined in claims 1 to 8; and the compound of formula (II) is of formulawherein R and R1have the same meaning as defined in claims 1 to 8.

10. The process according to any one of claims 1 to 9, wherein R1is a hydrogen atom or a Ci-4 alkoxyl group or a Ci-4 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H.

11. The process according to any one of claims 1 to 10, wherein R1is a hydrogen atom or a methyl group.

12. The process according to any one of claims 1 to 11, wherein R is a hydrogen atom or a Ci-4 alkoxyl group or a Ci-4 alkyl group optionally substituted by one or two of a hydroxy, a methoxy or a OC(O)H.

13. The process according to any one of claims 1 to 12, wherein the process for preparing compound of formula (I) comprises the step of a) reacting CH2=CH-CHR2-X with a compound of formulawherein R, R’, R1and R2have the same meaning as defined in claims 1 to 12; wherein Y is a halogen atom;Z is MgY or a halogen atom with the proviso that if Z is MgY then X is a halogen atom; or if Z is a halogen atom then X is MgY; to obtain a compound of formulawherein R, R’, R1and R2have the same meaning as defined in claims 1 to 12; and b) the oxidative cleavage of compound of formula (VI) as defined in claims1 to 12.

14. A compound of formulain the form of any one of its isomers or a mixture thereof; whereinR and R1, independently from each other, represent a hydrogen atom or a Ci- 6 alkoxyl group or a Ci-6 alkyl group optionally substituted by one or two of a hydroxy, Ci-6 alkoxyl or a OCHOR3group wherein R3is a hydrogen atom or a Ci-3 alkyl group; and provided that at least one group among R and R1is not a hydrogen atom; provided that R1is not a hydrogen atom when R is a C3-4 alkyl group ;R2represents a hydrogen atom or a methyl group;R’ is an hydrogen atom; orR and R’ are taken together and represent a C3-8 alkanediyl;Raand Rb, independently from each other, are a hydrogen atom or a C1-16 hydrocarbon group, optionally comprising one to three oxygen atoms or a group of formulain the form of any one of its isomers or a mixture thereof; R1, R2, R and R’ have the same meaning as defined above.

15. The compound according to claim 14, wherein the compound of formula (II) is of formula (IV)wherein R and R1have the same meaning as defined in claim 14.