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Enol ether properfume

A compound, alkyl technology, applied in the field of formula compounds, which can solve the problems of non-retention, lack of persistence, not very strong experience, etc.

Pending Publication Date: 2020-11-13
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, many actives which are particularly suitable for this type of application are known to lack tenacity on the laundry, or do not remain on the laundry when rinsed, with the result that their perfuming effect is only transient and not very intense experience

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] Example 1. (1-(octyloxy)prop-1-en-2-yl)benzene: diphenylpropanal (hydratropaldehyde) (10g, 74.5mmol), octanol (24.3g, 186mmol), A mixture of TsOH (0.28 g, 1.49 mmol) and toluene (100 mL) was heated at reflux for 1 h while removing the water of reaction with a Dean-Stark trap. After the mixture was cooled, it was diluted with EtOAc and washed with saturated NaHCO 3 and washed with saturated NaCl. Na for organic phase 2 SO 4 Dry, filter and concentrate to give crude dioctyl acetal. About a quarter (19.3mmol) of the material was mixed with KHSO 4 (0.5 g, 3.67 mmol) were mixed and heated under vacuum (30 torr) using a Kugelrohr distillation apparatus. After 2.5 hours at 140°C and an additional 2.5 hours at 160°C, GC analysis indicated that most of the acetal had been converted to the enol ether. Kugelrohr distillation (145 °C, 80 mTorr) afforded 3.46 g of enol ether (14.0 mmol, 73% yield) as a colorless liquid (E / Z=81:19). 1 H NMR (CDCl 3 , 500MHz, E-isomer): δ0.88(...

Embodiment 2～7

[0162] Examples 2-7. Dimethyl acetal (4 g, 22.1 mmol), alcohol (66 mmol) and KHSO 4 (33 mg, 0.22 mmol) for 1-2 hours to achieve the exchange of the methoxy group with the alcohol while removing the released methanol. Thereafter, the temperature is increased (120-140° C.) and the pressure is decreased (25-50 mTorr) to complete the elimination reaction to form the enol ether while removing excess alcohol. The enol ether was then distilled off from the reaction mixture (160-180°C, 25-50 mTorr). The product can be further purified by a second Kugelrohr distillation if desired.

Embodiment 2

[0163] Example 2. (1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)benzene: from (Z)-3-hexene-1- Starting from alcohol, the title compound was isolated as a colorless oil in 37% yield (E / Z=80:20).

[0164] 1 H NMR (CDCl 3 , 500MHz, E-isomer): δ0.97(t, J=7.5Hz, 3H), 1.99(d, J=1.3Hz, 3H), 2.07(pentet, J=7.3Hz, 2H), 2.41( q,J=7.0Hz,2H),3.83(t,J=7.0Hz,2H),5.33-5.40(m,1H),5.47-5.54(m,1H),6.46(q,J=1.3Hz,1H ),7.12-7.17(m,1H),7.24-7.32(m,4H).

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PUM

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Abstract

The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a ketone or aldehyde of formula(II), a formate ester of formula (III) and / or an alcohol of formula (IV) by exposing the compound of formula (I) to an environment wherein it is oxidized. Moreover, the present invention relates to aperfuming composition and a perfume consumer product comprising at least one compound of formula (I).

Description

technical field [0001] The present invention relates to compounds of formula (I) which are properfume compounds. In particular, the present invention relates to the release of ketones or aldehydes of formula (II), formates of formula (III) and / or alcohols of formula (IV) by exposing compounds of formula (I) to an environment which oxidizes them. compound method. Furthermore, the present invention relates to perfuming compositions and perfumery consumer products comprising at least one compound of formula (I). Background technique [0002] The fragrance (perfume) industry is particularly interested in compositions or additives capable of prolonging or enhancing the perfuming effect of mixtures of several fragrances simultaneously over a certain period of time. Achieving long-lasting performance is particularly desirable for standard fragrance raw materials, which are inherently too volatile or have poor substantivity, or deposit only a small amount on the end-use surface. ...

Claims

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Application Information

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IPC IPC(8): C07C43/166C07C43/168C11B9/00A61K8/33
CPCC07C43/168C07C43/166A61K8/33A61Q13/00A61Q5/12A61Q19/10A61Q5/02A61Q15/00A61K8/35C11B9/0053C11B9/0061
Inventor G·B·沃玛克B·因德拉达斯
Owner FIRMENICH SA
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