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Preparation method of L-N-ethyl-p-menthane-3-carboxamide compound

A technology of menthol amide and amine compound, applied in the field of preparation of L-menthol amide compound, can solve the problems of strong pungent smell, burning sensation, expensive menthol and the like, and achieve the effect of low price

Active Publication Date: 2017-07-14
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

L-menthol has the advantages of strong coolness, low threshold value and low price, but it also has some obvious disadvantages, such as strong pungent smell, bitter taste, not obvious cooling effect when the dosage is low, and when the concentration is large, there will be Burning sensation, strong volatility, short action time, etc. These shortcomings limit the application of L-menthol in many fields to a certain extent, especially chewing gum and some special types of cosmetics
[0008] The synthetic method reported at present all is starting raw material with L-menthol, yet the price of menthol is expensive, adds the Grignard reaction yield low (less than 50%), causes the price of menthyl amide class cooling agent on the market at present. too high

Method used

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  • Preparation method of L-N-ethyl-p-menthane-3-carboxamide compound
  • Preparation method of L-N-ethyl-p-menthane-3-carboxamide compound
  • Preparation method of L-N-ethyl-p-menthane-3-carboxamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Friedel-Crafts reaction

[0052] At 0-5°C, AlCl 3 (365g, 2.74mol) was added in 1000mL of nitromethane, passed into phosgene (542g, 5.48mol) and then insulated and stirred for 0.5 hour, then cymene (335g, 2.5mol) was added dropwise, and the dropwise process controlled the reaction temperature at 0 -5°C, after the dropwise addition, keep it warm for about 5 hours until no HCl gas is generated. After the reaction, remove excess phosgene and solvent, distill under reduced pressure, collect 67-70°C / 200pa fraction to obtain 2-isopropyl-5-methylbenzoyl chloride, 300g, yield 61%.

[0053] The analysis result of 2-isopropyl-5-methylbenzoyl chloride: 1H NMR (400MHz, CDCl 3 )δ7.93(s,1H),7.54(s,1H),7.43(s,1H),2.87(s,1H),2.42(s,3H),1.17(s,6H), HRMS(ESI)m / z[M+Na]+: calculated for[C 11 h 13 ClNaO]+: 219.0553. Found: 219.0540.

[0054] (2) Condensation reaction

[0055] At 0°C, 70wt% ethylamine aqueous solution (102g, 1.6mol) and 20wt% NaOH (320g, 1.6mol) aqueous solution w...

Embodiment 2

[0063] (1) Friedel-Crafts reaction

[0064] At 0-5°C, AlCl 3 (166g, 1.25mol) was added in 350mL dimethyl sulfoxide, passed into phosgene (542g, 5.48mol) and kept stirring for 0.5 hours, then added dropwise cymene (335g, 2.5mol), and the dropping process controlled the reaction temperature At 0-5°C, after the dropwise addition, keep the reaction for about 10 hours until no HCl gas is generated. After the reaction, remove excess phosgene and solvent, distill under reduced pressure, collect 67-70°C / 200pa fraction to obtain 2-isopropyl-5-methylbenzoyl chloride, 290g, yield 59%.

[0065] (2) Condensation reaction

[0066] At 0°C, 70wt% ethylamine aqueous solution (99g, 1.54mol) and 5wt% NaOH (1220g, 1.53mol) aqueous solution were mixed, then 2-isopropyl-5-methylbenzoyl chloride (300g, 1.5mol) was added dropwise ) in anisole solution (350 mL). After the reaction, wash with water (300mL*3), distill under reduced pressure, collect the 95-98℃ / 150pa fraction to obtain N-ethyl-2-isop...

Embodiment 3

[0072] (1) Friedel-Crafts reaction

[0073] At 0-5°C, AlCl 3 (666g, 5mol) was added in 3000mL nitrobenzene, passed into phosgene (742g, 7.5mol) and then insulated and stirred for 0.5 hour, then cymene (335g, 2.5mol) was added dropwise, and the reaction temperature was controlled at 0- 5°C, keep the reaction for about 2 hours after the dropwise addition until no HCl gas is generated. After the reaction, remove excess phosgene and solvent, distill under reduced pressure, collect 67-70°C / 200pa fraction to obtain 2-isopropyl-5-methylbenzoyl chloride, 304g, yield 62%.

[0074] (2) Condensation reaction

[0075]At 0°C, 70wt% ethylamine aqueous solution (191.2g, 3mol) and 40wt% NaOH (300g, 3mol) aqueous solution were mixed, followed by dropwise addition of 2-isopropyl-5-methylbenzoyl chloride (300g, 1.5mol) Methyl tert-butyl ether solution (3000mL). After the reaction, wash with water (300mL*3), distill under reduced pressure, collect the 95-98℃ / 150pa fraction to obtain N-ethyl-2...

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Abstract

The invention relates to a preparation method of an L-N-ethyl-p-menthane-3-carboxamide compound. The preparation method comprises the following steps: (1) Friedel-Crafts reaction: preparing 2-isopropyl-5-methyl benzoyl chloride from cymene and phosgene; (2) condensation reaction: under the effect of alkalis, reacting RNH2 with 2-isopropyl-5-methyl benzoyl chloride to prepare 2-isopropyl-5-methyl benzoyl amide, wherein R represents -Et or -CH2COOEt; and (3) reduction reaction: hydrogenating 2-isopropyl-5-methyl benzoyl amide to obtain reaction products containing the L-N-ethyl-p-menthane-3-carboxamide compound. The reactions products are subjected to distillation, rectification, melting, and crystallization to obtain N-ethyl-2-isopropyl-5-methylcyclohexanecarboxamide or L-N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester. The highest total yield is 18%, the raw material cost is reduced by 60%, compared with a conventional technology, and the cost advantage is obvious.

Description

technical field [0001] The invention relates to a preparation method of L-menthol amide compounds. Background technique [0002] Cooling agents are indispensable additives in people's daily life, and are widely used in the fields of food, daily chemicals, tobacco and medicine. For a long time, L-menthol has been the most familiar traditional cooling agent. L-menthol has the advantages of strong coolness, low threshold value and low price, but it also has some obvious disadvantages, such as strong pungent smell, bitter taste, not obvious cooling effect when the dosage is low, and when the concentration is large, there will be Burning sensation, strong volatility, short action time, etc. These shortcomings limit the application of L-menthol in many fields to a certain extent, especially chewing gum and some special types of cosmetics. Therefore, people begin to seek more effective cooling agent products. Among the many new cooling agents, the most prominent are N-ethyl-L-me...

Claims

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Application Information

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IPC IPC(8): C07C231/20C07C231/08C07C233/65
CPCC07B2200/07C07C51/58C07C231/02C07C231/08C07C231/20C07C233/65C07C63/68
Inventor 陈来中何勇周斌郭斌李剑锋张永振李文滨李晶孙烨
Owner WANHUA CHEM GRP CO LTD
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