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Fragrances with note of lily of the valley

A fragrance and aroma technology, applied in the field of new compounds, can solve the problem of reproducing the impression of natural lily of the valley flower aroma and smell

Active Publication Date: 2013-04-10
SYMRISE GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] However, none of the compounds (B) to (F) in the prior art was able to reproduce the fully composed odor impression of natural lily of the valley florals

Method used

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  • Fragrances with note of lily of the valley
  • Fragrances with note of lily of the valley
  • Fragrances with note of lily of the valley

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0334] Embodiment 1: the synthesis of 4-isopropyl cyclohexanol (IX)

[0335]

[0336] 1 kg of 4-isopropylphenol (the above formula (X)), 20 g of ruthenium carbon and 2.5 L of ethanol were charged into the autoclave. 4-Isopropylphenol was hydrogenated at 140°C for 6 hours at a hydrogen pressure of 40 bar. After filtration and removal of solvent, 1.04 kg of crude product was obtained with a purity of 99.8% (cis / trans isomer ratio 1:1, quantitative yield).

Embodiment 2

[0337] Example 2: Synthesis of 8-isopropyl-4-oxaspiro[4.5]decan-3-one (VIII)

[0338]

[0339] A mixture of 768 g of 4-isopropylcyclohexanol (5.40 mol, 4.50 eq, formula (IX) above) and 1.90 g of di-tert-butyl peroxide (13.0 mmol, 0.01 eq) was heated to 140°C. At this temperature, a mixture of 257 g of 4-isopropylcyclohexanol (1.80 mol, 1.50 eq) and 103 g of methyl acrylate (1.20 mol, 1.00 eq) was added dropwise over 6 hours. The low-boiling products formed were removed. Then 6.5 g of di-tert-butyl peroxide (44.0 mmol, 0.04 equiv) was added and stirred at 160° C. for another 2 hours. After cooling, 150 g of 10% sodium sulfite solution was added to the reaction mixture, and stirred at 60° C. for 1 hour. The phases were separated and the organic phase was washed with 100 g of water. After removal of the solvent, the crude product was purified by distillation. 102 g of (3R)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptane were isolated with a purity of 90% (cis / trans isome...

Embodiment 3

[0342] Example 3: Synthesis of 3-(4- Isopropylcyclohexen-1-yl)propanal (I)

[0343]

[0344] Catalyst preparation:

[0345] To a mixture of 34 g of cerium (III) acetate hydrate and 87 g of pumice was added 450 g of water. The mixture was stirred at 50 °C for 1 hour, then the water was removed in a rotary evaporator. A pyrolysis tube was filled with 35 g of prepared pumice (11 cm high) and heated at 440° C. for 1 hour.

[0346] Pyrolysis:

[0347] A mixture of 2 g of 8-isopropyl-4-oxaspiro[4.5]dec-3-one (93%, 9.5 mmol, formula (VIII) above) and 18 g of formic acid was charged at 440 °C in the presence of the above catalyst In the instrument, react in a nitrogen flow of 16 L / hour over 2 hours. The pyrolysis products were captured in a cooled trap, then diluted with MTBE and neutralized with saturated sodium bicarbonate solution. The phases were separated and the solvent was removed to obtain 1.5 g of crude product with a purity of 32%. This corresponds to a crude yi...

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Abstract

The invention describes a compound of formula (I)and use thereof as fragrance, especially as lily-of-the-valley fragrance and / or as an agent for increasing the substantivity and / or the retention of a fragrance preparation and / or as a fixative.

Description

technical field [0001] The present invention mainly relates to novel compounds selected from compounds of formula (Ia) [0002] [0003] and the compound of formula (Ib) [0004] [0005] And a mixture comprising the compound of the above formula (Ia) and the compound of the above formula (Ib) or a mixture consisting of the compound of the above formula (Ia) and the compound of the above formula (Ib). In addition, the present invention also relates to compounds of formula (I) [0006] [0007] Use as a fragrance, especially as a lily-of-valley fragrance, and fragrance preparations and perfuming products comprising a certain amount (preferably organoleptically effective) of the compound of formula (I) above, and the preparation of the above formula (I) (I) Compound method. Background technique [0008] Compounds with a floral odor are an integral part of the perfume industry as well as in cosmetics, body care products and cleaning products. A particularly valuabl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/225C11B9/00C07C45/00C07C43/303C07C45/59A61K8/33A61Q13/00A61Q19/00A61Q5/00A61Q5/02A61Q19/10A61Q5/12A61Q17/04A61Q5/10D06M13/13C11D9/26C11D9/44C11D3/20C11D3/50A61L9/01C11C5/00A61L101/32
CPCC11D3/50A61Q19/00C07C47/225A61K8/35A61Q15/00A61Q5/10A61Q19/10C07C2101/16A61Q5/12C11B9/0034C07C43/305A61Q5/02C07C47/11A61Q17/04C11C5/004A61Q5/065A61Q13/00C07C2601/16
Inventor 埃米莉·辛格贝恩德·霍尔舍
Owner SYMRISE GMBH & CO KG
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