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Method for synthesizing (S)(-)-gamma-lactone

A synthesis method and lactone technology are applied in the field of preparation of chiral synthetic fragrances, can solve problems such as no reports, and achieve the effects of improving economic value and improving aroma quality

Active Publication Date: 2006-12-06
APPLE FLAVOR & FRAGRANCE GRP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has been no report on the use of (R)-(+)-α-phenylethylamine for resolution, and there has been no report of the use of (R)-(+)-α-phenylethylamine for resolution. To obtain chiral 4-(S)-(-)-γ-decalactone, 4-(S)-(-)-γ-undecalactone and 4-(S)-(-)-γ-decalactone Dilactone's work

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0007] In a 50 ml three-necked flask, 2.4 g (60 mmol) of sodium hydroxide was dissolved in 20 ml of water, and 6.8 g (40 mmol) of racemic gamma-decalactone was added dropwise at 60°C, and Stirring was continued at temperature for 2 hours. After cooling to room temperature, add 20 ml of ethyl acetate, then dropwise add 20% sulfuric acid to adjust the acidity to P H =5. Extract and separate the organic layer, and extract twice with ethyl acetate. The organic layers were combined, and 2.4 g (20 mmol) of (R)-(+)-α-phenethylamine was added. The solution was cooled at -15 to -30°C for 48 hours to obtain 2.5 g of white crystals. Dissolve the crystals in 10 ml of water and heat to 90°C. When all the solids are dissolved, dilute sulfuric acid is added to obtain a hydroxy acid, which is further cyclized into a lactone. Extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, (S)-(-)-γ-decalactone was obtained after removing the solvent, the yield w...

example 2

[0009] In a 1000 ml three-necked flask, 38.4 g (960 mmol) of sodium hydroxide was dissolved in 320 ml of water, and 108.8 g (640 mmol) of racemic gamma-decalactone was added dropwise at 60°C, and Stirring was continued at temperature for 2 hours. After cooling to room temperature, add 320 milliliters of ethyl acetate, then dropwise add 20% sulfuric acid to adjust the acidity to P H =5. The organic layer was separated and extracted twice with ethyl acetate. The organic layers were combined, 128 ml of methanol was added, and 38.7 g (320 mmol) of (R)-(+)-α-phenethylamine were added. The solution was cooled at -22°C for 18.5 hours to obtain 65.0 g of white crystals. Dissolve the crystals in 100 ml of water and heat to 90°C. When all the solids are dissolved, dilute sulfuric acid is added to obtain the hydroxy acid, which is further cyclized into a lactone. Extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and (S)-(-)-γ-decalactone was ...

example 3

[0011] In a 1000 ml three-necked flask, 38.4 g (960 mmol) of sodium hydroxide was dissolved in 320 ml of water, and 108.8 g (640 mmol) of racemic gamma-decalactone was added dropwise at 60°C, and Stirring was continued at temperature for 2 hours. After cooling to room temperature, add 320 milliliters of ethyl acetate, then dropwise add 20% sulfuric acid to adjust the acidity to P H =5. The organic layer was separated and extracted twice with ethyl acetate. The organic layers were combined, 128 ml of methanol was added, and 38.7 g (320 mmol) of (R)-(+)-α-phenethylamine were added. The solution was cooled at -22°C for 67.5 hours to obtain 60.0 g of white crystals. The crystals were dissolved in 50 ml of water, heated to 80°C, and when the solid was completely dissolved, cooled to room temperature, and 55.0 g of solid was obtained by suction filtration.

[0012] Dissolve the recrystallized solid in an appropriate amount of water and heat to 90°C. When the solid is completely ...

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PUM

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Abstract

This invention discloses a method for synthesizing (S)-(-)-gamma-lactone. The method comprises: (1) using (R)-(+)-alpha-phenylethylamine as the chiral resolving agent, and reacting with racemic gamma-hydroxy acid to obtain a pair of diastereotopic salts; (2) separating by crystallization; (3) acidifying and cyclizing to obtain chiral (S)-(-)-gamma-lactone. (S)-(-)-gamma-lactone is (S)-(-)-gamma-decalactone, (S)-(-)-gamma-undercalactone or (S)-(-)-gamma-dodecalactone. (S)- (-)-gamma-lactone has special fragrance, and can be used to manufacture high-grade essence.

Description

Technical field: [0001] The invention relates to a preparation method of chiral synthetic perfume, in particular to a synthesis method of (S)-(-)-γ-lactone. Background technique: [0002] Natural lactone flavors are mostly found in the fruits of various fruits, such as γ-decalactone, γ-undecalactone, and γ-laurolactone, which are widely found in peaches, almonds, strawberries and other fruits. For example, the trade name of γ-undecalactone is also called peach aldehyde. They are all liquid in appearance and have a strong fruity aroma and milky aroma. They are widely used in the formulation of food flavors and daily cosmetic flavors. The chiral lactone after splitting has a purer and more natural style than the racemic lactone fragrance. For example: 4-(R)-(+)-γ-decalactone has a fresh peach flavor and can be used in fruit flavors. 4-(S)-(-)-γ-Decalactone can be used in dairy flavors. 4-(S)-(-)-γ-Undecalactone has a fatty feel and can be used in dairy flavors. 4-(S)-(-)...

Claims

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Application Information

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IPC IPC(8): C07D315/00C07D313/00
Inventor 冯黎吴世晖陶凤岗魏中浩胡勇成
Owner APPLE FLAVOR & FRAGRANCE GRP
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