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Process for preparing 4-methyl caprylic acid

A technology of methyl caprylic acid and methyl group, which is applied in the field of synthesis of spice 4-methyl caprylic acid, and achieves the effects of mild reaction conditions, high total yield and convenient post-treatment

Inactive Publication Date: 2009-09-09
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of this invention is to provide a kind of synthetic method of 4-methyl octanoic acid, this method is raw material with allyl alcohol, prepares 4-methanoic acid by four-step reaction base octanoic acid, so that the synthesis of 4-methyl octanoic acid not only solves the problem of raw material sources, but also is more economical

Method used

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  • Process for preparing 4-methyl caprylic acid
  • Process for preparing 4-methyl caprylic acid
  • Process for preparing 4-methyl caprylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0024] (1) At 0°C, after mixing 20.6 g (0.35 mol, 24.24 mL) allyl alcohol and 200 mL n-pentane, add dropwise to 1.6M n-butyllithium (0.80 mol, 500 mL) within 20 minutes, and stir at room temperature React for 1 hour. At 0°C, carefully add 200 mL of water to the reaction system, stir the reaction for 20 minutes, separate the layers, wash the organic layer with 30 mL of 3M hydrochloric acid, and then wash twice with 30 mL of water, dry the organic layer with anhydrous magnesium sulfate, filter, and spin the filtrate Most of the low-boiling point solvent was removed by evaporation, and then the product was distilled under reduced pressure to obtain 35 g (87%) of the product 2-methyl-1-hexanol (166-167° C. / 760 mm). The chemical purity measured by gas chromatography was >98%.

[0025] (2) At 0°C, 25.07 grams of methanesulfonyl chloride ( 0.22mol, 16.94mL), the dropwise addition was completed within 10 to 15 minutes, then stirred for 30 minutes, poured into ice water, separated in...

Embodiment 2

[0029] (1) At 0°C, after mixing 58.08 grams (1.00mol, 69.26mL) of allyl alcohol and 600mL of n-pentane, they were added dropwise to 1.2M n-butyllithium (2.50mol, 2083mL) within 30 minutes, and stirred at room temperature React for 1 hour. At 0°C, carefully add 600 mL of water to the reaction system, stir the reaction for 30 minutes, separate the liquids, wash the organic layer with 260 mL of 1M hydrochloric acid, then wash twice with 90 mL of water, dry the organic layer with anhydrous magnesium sulfate, filter, and the filtrate is rotovapped Most of the low-boiling point solvent was removed, and the residue was distilled under reduced pressure to obtain 98.8 g (85%) of the product 2-methyl-1-hexanol (166-167° C. / 760 mm). The chemical purity measured by gas chromatography was >98%.

[0030] (2) At 0°C, add 80 mL of dichloromethane and p-methanol dropwise to a mixed solution of 23.2 grams (0.2 mol) of 2-methyl-1-hexanol, 150 mL of dichloromethane, and 42 mL (0.3 mol) of trieth...

Embodiment 3

[0034] (1) At 0°C, add 108.28 g (0.40 mol) of phosphorus tribromide dropwise to 116.2 g (1.0 mol) of 2-methyl-1-hexanol, and the dropwise addition is completed within 30 minutes, then stir at room temperature for 15 hours , the reactant was poured into ice water, separated into layers, and the water layer was removed. The organic layer was washed twice with 5 mL of concentrated sulfuric acid, washed twice with 20 mL of water, and washed with 20 mL of saturated sodium carbonate solution. The organic layer was dried with anhydrous magnesium sulfate and filtered. The residue was distilled under reduced pressure to obtain 89.55 g (50%) of the product 2-methyl-1-bromohexane.

[0035] (2) 13.72 g (0.4 mol) of 70% sodium hydride was washed with toluene to remove mineral oil, put in a flask, added 400 ml of toluene, and 64.03 g (0.4 mol, 60.70 mL) of diethyl malonate was added dropwise with stirring ), the reaction emits hydrogen, until no gas is released, add phase transfer catalyst ...

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Abstract

The invention relates to a preparation method for 4-methyl caprylic acid. The method comprises the following steps: allyl alcohol is taken as the raw material and the key intermediate 2-methyl-1-hexanol and the derivative are synthesized; diethyl malonate loses a proton under the effect of alkali and undergoes the nucleophilic substitution reaction with a series of 2-methyl-1-hexanol derivatives, thus obtaining the product 2-(2-methyl hexyl) diethyl malonate and then 4-methyl caprylic acid through saponification, decarboxylation, saponification and acidification. Compared with the prior art, the method has the advantages of available materials, small amount of catalyzer, high yield and low production cost, thus having higher industrialization value.

Description

technical field [0001] The present invention relates to the synthesis of perfume 4-methyl octanoic acid. Background technique [0002] 4-methyl caprylic acid naturally exists in tea, jackfruit, rum, apples, and strawberries, and is a natural equivalent spice. Its aroma is characterized by waxy pork, beef, and roasted lamb fat aromas, as well as cream, milk, and lactone aromas. Taste characteristics are manifested in the concentration of 20mg / kg, with fat, waxy, creamy, lactone flavor and metallic smell. 4-Methyloctanoic acid is widely used and can be used in dairy products, cheese, butter, butter oil and condensed milk. The dosage (usually / maximum, mg / kg) is as follows: frozen dairy products: 0.15 / 3.0; meat products: 0.1 / 0.5; jelly, pudding: 0.05 / 0.15; soup: 0.05 / 0.15; fast food: 1.0 / 3.0; gravy: 0.15; milk products: 0.3 / 3.0; cheese: 0.3 / 3.0. Therefore, people are very interested in how to produce 4-methyloctanoic acid in large quantities. [0003] There are some bibliog...

Claims

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Application Information

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IPC IPC(8): C07C53/126C07C51/09C07C51/38C07C27/02C11B9/00
Inventor 刘旭东赵兴韦刘锎扬周跃
Owner UNIV OF SCI & TECH BEIJING
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