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Process for the preparation of polysantol-type compounds

A technology of compounds and mixtures, applied in the field of new formula compounds and new intermediates in a method, can solve the problems of industrial scale expansion and lengthy

Active Publication Date: 2019-01-11
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, industrial scale-up of this step can be lengthy, and the difficulties encountered by the authors in eliminating the obtained alcohols have biased this route

Method used

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  • Process for the preparation of polysantol-type compounds
  • Process for the preparation of polysantol-type compounds
  • Process for the preparation of polysantol-type compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of (R,E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-one

[0063] a) 3,3-Dimethyl-4-oxo-1-((R)-2,2,3-trimethylcyclopent-3-en-1-yl)pent-2-yl acetate

[0064] In a 2-liter flask, stir 4-hydroxy-3,3-dimethyl-5-((R)-2,2,3-trimethylcyclopent-3-en-1-yl)pentyl -2-one (267 g) and 440 mL cyclohexane. Add DMAP (6.0g, 49mmol) and Et 3 After N (100 g, 0.98 mol), Ac was added within 20 minutes 2 O (94 g) (exothermic reaction to 50°C). The mixture was heated at 86 °C, and 31 g of Ac 2 O. After 75 minutes at 86°C, the mixture was cooled to 10°C. Add 581 g of 10% H 3 PO 4 Aqueous solution, after stirring (10 min), the organic phase (774 g) was separated and washed with 50 g water, 25 g water and 25 g saturated aqueous NaCl. Saturated with 50g NaHCO 3 After washing with aqueous solution, the organic mixture was distilled (30 °C-104 °C / 0.1 mbar) to obtain 243.6 g (74.7%) of acetic acid 3,3-dimethyl-4-oxo-1-((R)-2,2 ,3-Trimethylcyclopent-3-en-...

Embodiment 2

[0070] Preparation of (R,E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-one-p Proportion

[0071] a) Dehydration under acidic conditions

[0072] In 0.2g KHSO 4 In the presence of 2 g of 4-hydroxy-3,3-dimethyl-5-((R)-2,2,3-trimethyl cyclopent-3-en-1-yl)pentan-2-one. 1.6 g of (R)-Bornolenal (80% purity) were obtained. No trace of the desired product (R,E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-ene was detected in either the distillation product or the residue -1-yl)pent-4-en-2-one.

[0073] b) Dehydration under acidic conditions

[0074] at 0.67 g (3.61 mmol) of pTsOH·H 2 2 g of 4-hydroxy-3,3-dimethyl-5-((R)-2,2,3-trimethylcyclopent-3-ene- 1-yl)pentan-2-one. After 60 minutes, complete conversion was observed and no trace of the desired product (R,E)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3 -en-1-yl)pent-4en-2-one (only the formation of (R)-borneol was observed).

[0075] Dehydration under acidic conditions did not provide the desired p...

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Abstract

The present invention relates to the field of organic synthesis and more specifically it concerns a novel compound of formula (I) which could be used as a novel intermediate in the process for the preparation of compound of formula (III).

Description

technical field [0001] The present invention relates to the field of organic synthesis, more specifically, to a novel compound of formula (I), which can be used as a novel intermediate in the process for preparing the compound of formula (III). Background technique [0002] Sandalwood ingredients such as (trademark from Firmenich SA), is a very popular fragrance ingredient. Typically, they are synthesized by aldol condensation reactions starting with aldehydes such as α-borneol. especially, It is obtained by aldol condensation between α-borneol and ethyl methyl ketone followed by methylation and reduction. There are several disadvantages to this synthetic route; namely, the regioselectivity of the first step of the synthesis is challenging, and by-products are formed during the methylation step, which requires the use of methyl chloride. [0003] Much effort has been made to improve each step of this route or even via different intermediates. In Tetrahedron Lett.2004,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/52C07C49/20C11B9/00
CPCC11B9/0019C11B9/0026C07C67/08C07C69/14C07C69/145C07C69/24C07C45/65C07C45/72C07C2601/10C07C2601/14C07C2601/16C07C49/21C07C49/242C07C49/172
Inventor O·克诺普夫
Owner FIRMENICH SA