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Process for the preparation of beta-gamma ene carbonyl derivatives

一种衍生物、烃基的技术，应用在β-γ烯羰基衍生物的制备领域，能够解决增加收率等问题

Active Publication Date: 2009-03-18
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Indeed, beta-gamma unsaturated ketones or esters can serve as useful intermediates in the preparation of important compounds, but there is still a need for new or alternative methods for their synthesis with good selectivity and thus increased yields

Method used

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  • Process for the preparation of beta-gamma ene carbonyl derivatives
  • Process for the preparation of beta-gamma ene carbonyl derivatives
  • Process for the preparation of beta-gamma ene carbonyl derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] A) General procedure

[0083] In the presence of magnesium 2-ethylhexanoate (0.045 mol) and 2-ethylhexanoic acid (0.24 mol), the starting compound (II) (obtained according to the literature) (0.24 mol) (see Table 4) was heated at 160°C Heat for 10-9 hours. After cooling at 50℃, the mixture uses 10gH 2 SO 4 20% washing, vacuum distillation to give unsaturated esters. Table 4 shows the yield and different isomers of compound (I).

[0084] Table 4

[0085]

Compound (II)

Compound (I)

Yield

(%)

Isomer ratio

PhCHMeCH=C(COOMe) 2

Methyl 4-phenyl-3-pentenoate

80

β-γ / α-β=49

(E)-β-γ / (Z)-β-γ=5.3 / 1 [2-Methyl-4-(2,6,6-trimethyl

-1-Cyclohexen-1-yl)butylene)propane

Dimethyl Diacid 4-methyl-6-(2,6,6-trimethyl

-1-cyclohexen-1-yl)-3-hexene

Methyl acid 90

β-γ / α-β=49

(E)-β-γ / (Z)-β-γ=5.1 / 1

[0086] B) General procedure

[0087] Same as the above experimental procedure, using [2-methyl-4-(2,6,6-trimethyl-1-cyclo...

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Abstract

The present invention relates to a preparation of beta-gamma ene carboxylic or ketone derivatives, which may also have particular requirement on the configuration of the carbon-carbon double bond. The method requires a thermal treatment of alpha-beta unsaturated malonate or acetylacetonate derivatives in the presents of at least one carboxylic acid and at least one alkaline, alkaline-earth or lanthanide halide or carboxylates.

Description

Technical field [0001] The present invention relates to the field of organic chemistry, and more particularly, to the preparation of β-γ ene carbonyl derivatives, which can also have special requirements in the configuration of carbon-carbon double bonds. Background technique [0002] The preparation of three or four substituted β-γ unsaturated esters or ketone derivatives by elimination reaction on the acyl or carboxylic acid esters of α-β unsaturated gem dicarbonyl derivatives has only been reported in one literature (see V. Venkateswaran Et al., Tetrahedron Letters, 1979, 553). [0003] In this article, the author reports the reaction based on the following scheme: [0004] [0005] However, with this method, the author obtains products in which the main isomer is an α-β unsaturated derivative in two cases (contrary to the present invention), and in one case where the main isomer is β -The product of γ unsaturated derivatives, but with weak selectivity. [0006] K. Schulte-E...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/32C07C69/618C07C403/20
CPCC07C45/676C07C67/32C07C2101/16C07C2601/16C07C69/618
Inventor 于贝尔·米蒙塞尔日·博诺代
Owner FIRMENICH SA