Preparation method of pulegone derivative

A technology of menthone and derivatives, which is applied in the field of derivatization and preparation of 5-methyl-2-(1-methylethylene)cyclohexanol, which can solve the problems of expensive and difficult raw material sources, and achieve product yield High, good optical purity, simple operation effect

Pending Publication Date: 2016-11-23
安徽爱有澄生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the existing reports, about the method of preparing 5-methyl-2-(1-methylethylene) cyclohexanol with menthone as raw material, most of them are catalyzed by Et2SiH2/(Ph3P)3RhCl Reduction (Ionic and organometallic-catalyzed organosilane re

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  • Preparation method of pulegone derivative

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Effect test

Embodiment 1

[0010] 1) At 0°C, add 250ml of anhydrous methanol and 15.2g of menthone to a single-necked flask, stir for 15 minutes, then add 11.3g of sodium borohydride. After feeding, seal the flask with a balloon and keep it at 0°C for 3 hours , point the board to detect that the long-leaved menthol has reacted completely, stop the reaction; dilute the sodium borohydride with hydrochloric acid solution until no bubbles emerge, distill methanol and extract three times with 100ml dichloromethane, combine dichloromethane, dry, After concentration, 14.3 g of 5-methyl-2-(1-methylethylene)cyclohexanol was obtained, with a yield of 92.6%.

[0011] 2) In a constant temperature shaker, with a 200ml blue bottle as a reaction vessel, add 60ml of toluene, 7.7g of 5-methyl-2-(1-methylethylene) cyclohexanol, 10.0g of p-chlorophenol B Ester, 0.3g of porcine pancreatic lipase PPL, 1.5g of acid resin D006, after feeding, the temperature was raised to 35°C for reaction, after 11 hours, the detection of 5-...

Embodiment 2

[0015] 1) At 0°C, add 1000ml of anhydrous methanol and 152g of menthone to a single-necked flask, stir for 20 minutes, then add 150g of sodium borohydride, seal the flask with a balloon, keep at 0°C for 4 hours, TLC Detect that the long-leaf menthol has reacted completely, stop the reaction; dilute the sodium borohydride with hydrochloric acid solution until no more bubbles emerge, distill the methanol and extract three times with 300ml ethyl acetate, combine the ethyl acetate, dry, and concentrate 143.8 g of 5-methyl-2-(1-methylethylene)cyclohexanol was obtained, with a yield of 93.4%.

[0016] 2) In a constant temperature shaker, with a 1000ml blue cap bottle as a reaction vessel, add 700ml of toluene, 77g of 5-methyl-2-(1-methylethylene) cyclohexanol, and 110g of p-chlorophenol acetate , 3g of porcine pancreatic lipase PPL, 10g of acidic resin D006, after feeding, the temperature was raised to 40°C for reaction. After 12 hours, it was detected that 5-methyl-2-(1-methylethyl...

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Abstract

The invention discloses a method for deriving an optical purity hydroxy compound by taking pulegone as a raw material. The pulegone is reduced by a hydrogenating reagent to obtain 5-methyl-2-(1-methylethylene) cyclohexanol, and the 5-methyl-2-(1-methylethylene) cyclohexanol is split to obtain (1R)-5-methyl-2-(1-methylethylene) cyclohexanol. Prochiral ketone in the pulegone is basically changed into a chiral center and further split. The method has the advantages of simplicity in operation, high product yield, fine optical purity and the like.

Description

technical field [0001] The present invention relates to a preparation method of optical pure chiral hydroxylation, especially the preparation method of (1R)-5-methyl-2-(1-methylethylidene)cyclohexanol derived from longifolin as raw material method. Background technique [0002] Menthone is a ketone synthetic spice, mainly used as blending spices for flavors such as mint, lavender and rose, and also used for geranium oil and the like. At the same time, it is also a latent chiral compound, and its ketone group can be reduced to obtain the corresponding chiral alcohol, which can be further resolved to obtain an optically active chiral hydroxyl compound. [0003] In the existing reports, about the method of preparing 5-methyl-2-(1-methylethylene) cyclohexanol with menthone as raw material, most of them are catalyzed by Et2SiH2 / (Ph3P)3RhCl Reduction (Ionic and organometallic-catalyzed organosilane reductions, Organic Reactions (Hoboken, NJ, United States), 71, 1-737; 2008), whi...

Claims

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Application Information

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IPC IPC(8): C12P7/22
CPCC12P7/22
Inventor 褚晓晨
Owner 安徽爱有澄生物科技有限公司
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