Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process for producing wine lactone

a technology of wine lactone and process, applied in the field of process for producing wine lactone, can solve the problems of not being suitable for industrial use, not cost-effective for producing all stereoisomers, and difficult to use process starting from limonene on an industrial scal

Inactive Publication Date: 2013-09-19
TAKASAGO INTERNATIONAL CORPORATION
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a simple and efficient method for producing wine lactone without using harmful or expensive reagents and without extreme reaction conditions. Additionally, this method allows for highly selective production of wine lactone. The production process involves a cyclization reaction of a specific compound, which can be performed using either specific conditions or simple chemical reactions. This process is suitable for industrial scale production.

Problems solved by technology

However, the process for producing all stereoisomers is not cost-effective because wine lactone, i.e., the (3S,3aS,7aR) isomer which is excellent in aroma and the quality thereof is obtained in a yield as low as 20%.
The process mediated by Diels-Alder reaction allows diastereoselective synthesis of a desired stereoisomer, but is not suitable for use on an industrial scale because of using harmful reagents, such as chromic acid for oxidation reaction and methyl iodide for methylation.
The process starting from limonene is also difficult to use on an industrial scale because of using harmful reagents, such as chromic acid for oxidation reaction.
According to this process, it is possible to synthesize wine lactone in a diastereoselective manner, but this process is not suitable for use on an industrial scale because of great difficulty in obtaining the starting 2-cyclohexenol derivative and because of using harmful reagents, such as methyl iodide for methylation.
However, this process requires the stages of lactonization, lactone opening and recyclization, and hence involves a larger number of steps and complicated procedures.
Moreover, this process is not suitable for use on an industrial scale because of using harmful reagents, such as methyl iodide for methylation.
However, this process is not suitable for use on an industrial scale because of using harmful reagents, such as chromic acid for oxidation reaction.
However, this process also has a problem in using harmful reagents, such as butyl lithium and methyl iodide for methylation.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for producing wine lactone
  • Process for producing wine lactone
  • Process for producing wine lactone

Examples

Experimental program
Comparison scheme
Effect test

first embodiment

1. First Embodiment

[0065]The production process according to the first embodiment of the present invention is characterized by comprising step A), step B-1) and step C):

[wherein R1 is an alkyl group containing 1 to 4 carbon atoms, R2 is an alkyl group containing 1 to 4 carbon atoms, and X is a chlorine atom or a bromine atom].

[0066]Detailed explanation will be given below for each step.

(1) Step A)

[0067]Step A) is intended to react a β-keto ester represented by formula (1):

[wherein R1 is an alkyl group containing 1 to 4 carbon atoms]

with a 2-halo ester represented by formula (2):

[wherein R2 is an alkyl group containing 1 to 4 carbon atoms, and X is a chlorine atom or a bromine atom]

under basic conditions to thereby obtain a 2-aceto-3-methyl-succinic acid ester represented by formula (3):

[wherein R1 is as defined in formula (1), and R2 is as defined in formula (2)].

[0068]In the above formulae, R1 and R2, which may be the same or different, are each an alkyl group containing 1 to 4 car...

second embodiment

2. Second Embodiment

[0209]The production process according to the second embodiment of the present invention comprises step A), step B-2), step B-3) and step C):

[wherein R1 is an alkyl group containing 1 to 4 carbon atoms, R2 is an alkyl group containing 1 to 4 carbon atoms, and X is a chlorine atom or a bromine atom].

[0210]Among the above steps in the second embodiment, step A) and step C) are the same as those of the first embodiment and their explanation will be omitted. Detailed explanation will be given below for step B-2) and step B-3).

(1) Step B-2)

[0211]Step B-2) is intended to react the 2-aceto-3-methyl-succinic acid ester obtained in step A) with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to thereby obtain an α-methyl-γ-keto acid ester represented by formula (5):

[wherein R2 is as defined in formula (2)].

[0212]Methyl vinyl ketone used in this reaction may be either a commercially available product or a synthetic product, as described abo...

third embodiment

3. Third Embodiment

[0236]The production process according to the third embodiment of the present invention comprises step A), step B-2) and step E):

[wherein R1 is an alkyl group containing 1 to 4 carbon atoms, R2 is an alkyl group containing 1 to 4 carbon atoms, and X is a chlorine atom or a bromine atom].

[0237]Among the above steps in the third embodiment, step A) is the same as that of the first embodiment, while step B-2) is the same as that of the second embodiment. Thus, their explanation will be omitted. Detailed explanation will be given below for step E).

(1) Step E)

[0238]In a first case, step E) is intended for reduction reaction of the α-methyl-γ-keto acid ester obtained in step B-2) in the presence of a ruthenium complex selected from compounds represented by formula (6) or (7) and in the presence of a hydrogen donor to thereby obtain a compound represented by formula (a):

[0239]The ruthenium complexes represented by formulae (6) and (7) may be the same as those explained i...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to a method comprising (A) reacting a β-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an α-methyl-γ-keto acid; and (C) reducing the resulting α-methyl-γ-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof. Alternatively, the present invention relates to a method comprising step (A) as recited above; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to obtain an α-methyl-γ-keto acid ester; and (E) reducing the resulting α-methyl-γ-keto acid ester in the presence of a ruthenium complex having a specific structure and in the presence of a hydrogen donor to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a Divisional of U.S. application Ser. No. 13 / 483,373, filed May 30, 2012, which claims priority from Japanese patent application no. JP 2011-123267, filed Jun. 1, 2011, the entire contents of which are incorporated herein by reference.TECHNICAL FIELD[0002]The present invention relates to a process for producing wine lactone, which is useful as a flavor or fragrance compound, or a stereoisomer thereof or a mixture thereof.BACKGROUND ART[0003]Wine lactone, whose chemical name is (3a,4,5,7a)-tetrahydro-3,6-dimethyl-benzofuran-2(3H)-one, was found in 1975 by Southwell from metabolites in koalas. This compound was isolated from white wine in 1996 by Guth as being one of the most important aroma components of white wine and thus named as “wine lactone.” Wine lactone has eight types of stereoisomers, all of which were synthesized by Guth, and the compound naturally occurring (i.e., wine lactone) is a (3S,3aS,7aR) isomer. Amon...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): C07D307/83
CPCC07D307/77C07D307/83
Inventor YAGI, KENJIKOMATSUKI, YASUHIROUJIHARA, HIDEOISHIDA, KENYA
Owner TAKASAGO INTERNATIONAL CORPORATION
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com