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4-Method for synthesizing 4-Methyloctanoic Acid

A technology of methyl octanoic acid and a synthesis method, which is applied in the preparation of carboxylate/lactone, organic chemistry, etc., can solve the problems of high preparation cost, high difficulty, rare raw materials, etc., and achieves reduced difficulty, mild reaction conditions, and high yield. rate effect

Active Publication Date: 2012-07-25
黄山科宏生物香料股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The disadvantages of the above method are: the first step hydrogenation reduction requires high temperature and high pressure, and the raw materials are rare; the second step halogenation reaction is carried out under the condition of hydrogen iodide, the preparation cost is high and the difficulty is great

Method used

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  • 4-Method for synthesizing 4-Methyloctanoic Acid
  • 4-Method for synthesizing 4-Methyloctanoic Acid
  • 4-Method for synthesizing 4-Methyloctanoic Acid

Examples

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Embodiment 1

[0015] Embodiment 1: the synthesis of 4-methyl-butylactone

[0016] In a 2L flask equipped with a mechanical stirrer, a thermometer, an addition funnel and a reflux condenser, add 48g (2mol) of magnesium shavings, 150mL of diethyl ether and a grain of iodine. Start stirring, add dropwise a mixture of 274g bromobutane (2mol) and 300mL diethyl ether, keep the reaction slightly boiling, complete the addition in about 2 hours, and then keep the temperature at 40°C for 1 hour. Cool the reaction liquid to -5°C, add dropwise a mixture of 260g methyl levulinate (2mol) and 150mL diethyl ether, and control the reaction temperature below 0°C. After the addition, stir at room temperature for 2 hours, carefully add 416g of saturated ammonium chloride aqueous solution to decompose, control the temperature at 10°C, and generate granular solid and almost dry ether layer. Pour off the ether layer, extract the solid with 2*250mL ether, distill the crude product under reduced pressure after dee...

Embodiment 2

[0017] Embodiment 2: the synthesis of 4-methyl-butylactone

[0018] In a 1L flask equipped with a mechanical stirrer, a thermometer, an addition funnel and a reflux condenser, add 24 g (1 mol) of magnesium shavings, 75 mL of diethyl ether and a grain of iodine. Start stirring, add dropwise a mixture of 140 g of bromobutane (1 mol) and 150 mL of diethyl ether, keep the reaction slightly boiling, complete the addition in about 2 hours, and then keep the temperature at 40°C for 1 hour. Cool the reaction liquid to -15°C, add dropwise a mixture of 156g methyl levulinate (1.2mol) and 150mL diethyl ether, and control the reaction temperature below -10°C. After the addition, stir at room temperature for 2 hours, carefully add 208 g of saturated ammonium chloride aqueous solution to decompose, control the temperature at 10 ° C, and generate granular solid and almost dry ether layer. Pour off the ether layer, extract the solid with 2*125mL ether, distill the crude product under reduced...

Embodiment 3

[0019] Embodiment 3: the synthesis of 4-methyl-butylactone

[0020] In a 2L flask equipped with a mechanical stirrer, a thermometer, an addition funnel and a reflux condenser, add 24 g (1 mol) of magnesium alloy, 100 mL of tetrahydrofuran, benzene (tetrahydrofuran:benzene=1:1) and a grain of iodine. Start stirring, add dropwise a mixture of 140g of bromobutane (1mol) and 200mL of tetrahydrofuran and benzene, keep the reaction temperature at about 45°C, complete the addition in about 2 hours, and then keep the temperature at 45°C for 1 hour. Cool the reaction liquid to -10°C, add dropwise a mixture of 156g of methyl levulinate (1.2mol) and 150mL of tetrahydrofuran and benzene, and control the reaction temperature below -5°C. After the addition, stir at room temperature for 2 hours, carefully add 350g of 10% hydrochloric acid to decompose, control the temperature at 10°C, wash the base layer with water until neutral, remove the solvent and distill the crude product under reduced...

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Abstract

The invention relates to a method for synthesizing 4-Methyloctanoic Acid. Firstly, an intermediate of 4-methyl-5-octanolide is obtained by grignard reaction of 4-Oxovaleric acid methyl ester with 1-bromobutyl-magnesium halide, the intermediate of 4-methyl-5-octanolide and calcium sulfate for dehydroxylation to generate 4-Methyl-Octenoic acid, and the 4-Methyl-Octenoic acid is catalytically hydrogenated to obtain the target product. Compared with prior art, the raw material of the method is easy to get, the method need not high-temperature and high pressure environment, the reaction condition is moderate, and the method reduces production cost and difficulty, simultaneously obtains high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to a synthesis process of fine chemical raw materials, and more specifically relates to a synthesis method of 4-methyl octanoic acid. Background technique [0002] 4-Methyl caprylic acid naturally exists in mutton, boiled mutton, roast mutton, mutton liver and suet, etc. It has a woody aroma and animal smell, and is an important component of mutton flavor essence. In 1941, P.A.LEVENE (P.A.LEVENE, and MARTIN KUNA, J.Biol.Chem., 141, 255, 1941) etc. reported the following synthetic method: 1) 2-methylheptanoic acid ethyl ester was hydrogenated to prepare 2-methylheptanol ; 2) the above-mentioned intermediate reacts with hydrogen iodide to prepare 2-methyl-1-iodoheptane; 3) the above-mentioned intermediate reacts with diethyl malonate, and the target product is obtained through hydrolysis and decarboxylation. [0003] The disadvantages of the above method are: the first step of hydrogenation reduction requires high temperature and h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C53/126C07C51/09
Inventor 程存照
Owner 黄山科宏生物香料股份有限公司
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