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Method for preparing carvacrol with 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

A technology of isopropenyl and cyclohexanone, applied in the field of chemistry, can solve the problems of difficulty in wastewater treatment, large addition amount, and high equipment requirements, and achieve the effects of high yield, convenient operation and good quality.

Active Publication Date: 2017-06-09
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses acid as the main catalyst, and the addition amount is relatively large, which requires high equipment, and the post-treatment also needs to be neutralized with lye, which will inevitably produce a large amount of waste water, which brings great difficulties to waste water treatment.

Method used

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  • Method for preparing carvacrol with 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone
  • Method for preparing carvacrol with 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 4.0mL of toluene, 1.4g of phosphorus pentoxide, 2.0g of 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone in sequence in a 15mL round bottom flask, and heat the oil bath to 98-108°C , kept under stirring for 2.5 hours, after TLC detected that all L-carveol disappeared, stop the reaction, cool to room temperature, add 1mL of water, oscillate, stand still, and separate the water layer. The aqueous layer was extracted with 1 mL of ethyl acetate, and the organic phases were combined. The organic phase was sequentially saturated with sodium bicarbonate solution to pH = 7-8, then washed with water to pH = 7-7.5, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 1.39 g of carvacrol with a yield of 78 %. 1 H NMR (400mHz, CDCl 3 ): δ1.26(d, 6H, J=6.8Hz), 2.27(s,3H), 2.83-2.90(m, 1H), 5.33(s, 1H), 6.71(d, 1H, J=1.7Hz) ,6.77(dd, 1H, J=7.6Hz, 1.7Hz), 7.08(d, 1H, J=7.6Hz) (such as figure 1 ). 13 C-NMR (100mHz, CDCl 3 ): δ15.4, 24...

Embodiment 2

[0024] 4.0 mL of toluene, 1.0 g of phosphorus pentoxide, and 2.0 g of 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone were sequentially added to a 15 mL round bottom flask. Heat the oil bath to 98-108°C, and keep it under stirring for 1.5 hours. After TLC detected that all the L-carveol disappeared, stop the reaction, cool to room temperature, add 1 mL of water, shake, stand still, and separate the water layer. The aqueous layer was extracted with 1 mL of ethyl acetate, and the organic phases were combined. The organic phase was washed successively with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 1.25 g of carvacrol with a yield of 70%. All the other implementations are as in Example 1.

Embodiment 3

[0026] 4.0 mL of 1,4-dioxane, 1.4 g of phosphorus pentoxide, and 2.0 g of 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone were sequentially added to a 15 mL round bottom flask. Heat the oil bath to 98-108°C and react for 2.0 hours. Stop the reaction, cool to room temperature, add 1 mL of water, shake, let stand, and separate the water layer. The aqueous layer was extracted with 1 mL of ethyl acetate, and the organic phases were combined. The organic phase was washed successively with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 1.44 g of carvacrol with a yield of 81%. All the other implementations are as in Example 1.

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Abstract

The invention discloses a method for preparing carvacrol from 2-hydroxy-5-isopropenyl-2-methylcyclohexanone. The method uses 2-hydroxy-5-isopropenyl-2-methylcyclohexanone as a raw material and carries out intramolecular dehydration and intramolecular rearrangement in an organic solvent with phosphoric pentoxide as a dehydrating agent to prepare carvacrol. The method comprises the following concrete steps: (1) successively adding the organic solvent, phosphoric pentoxide and 2-hydroxy-5-isopropenyl-2-methylcyclohexanone into a reactor provided with a stirring device, carrying out stirring, then heating the obtained mixture to 98 to 108 DEG C, carrying out a reaction for 1 to 3 h with the temperature maintained, then cooling a reaction product to room temperature (in a range of 20 to 30 DEG C), washing the reaction product with water and then carrying out layering so as to separate a water layer; (2) extracting the water layer with ethyl acetate and combining organic phases; and (3) washing the combined organic phase with a saturated sodium bicarbonate solution and clear water in sequence, then drying the organic phase with anhydrous sodium sulfate and carrying out silica gel column chromatographic separation so as to obtain carvacrol. The method provided by the invention has the advantages of convenience in operation, mild reaction conditions, high yield, good product quality, etc.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a method for preparing carvacrol with 2-hydroxy-5-isopropenyl-2-methyl-cyclohexanone. [0002] technical background [0003] Carvacrol is an important product used in the fields of food additives, spices, antioxidants, insect repellants, sanitation fungicides, preservatives, deodorants, pharmaceutical intermediates, etc. The market prospect is very broad. In addition, carvacrol is also Main active ingredient of natural oregano oil. Oregano oil is a feed additive approved by the Ministry of Agriculture of my country. It is a safe, efficient, green and non-incompatible traditional Chinese medicine additive. [0004] Carvacrol, also known as 2-methyl-5-isopropylphenol, is a colorless to light yellow thick oily liquid with thymol odor. Its structural formula is: [0005] Currently, there are two main methods for the synthesis of carvacrol. The U.S. invention patent US Patent 2064885 intr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/07C07C37/07C07C37/68
CPCC07C37/07C07C37/685C07C39/07
Inventor 刘晓涛周云兵张飞王坤朱延法万猛
Owner HUAIAN WAN BANG SPICE IND CO LTD