71804-27-8

Basic information

• Product Name: (+)-8-PHENYLMENTHYL CHLOROACETATE
• Synonyms: (+)-8-PHENYLMENTHYL CHLOROACETATE;(1R,2S,5R)-(+)-5-METHYL-2-(1-METHYL-1-PHENYLETHYL)CYCLOHEXYL CHLOROACETATE;(1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl;(1R,2S,5R)-(+)-5-METHYL-2-(1-METHYL-1-PH ENYLETHYL)CYCLOHEXYL CL-ACETATE, 99%;Acetic acid, chloro-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS NO: 71804-27-8
• Molecular Formula: C₁₈H₂₅ClO₂
• Molecular Weight: 308.84
• Mol File: 71804-27-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 385.281°C at 760 mmHg
• Flash Point: 188.265°C
• Appearance: /
• Density: 1.084g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: (+)-8-PHENYLMENTHYL CHLOROACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-8-PHENYLMENTHYL CHLOROACETATE(71804-27-8)
• EPA Substance Registry System: (+)-8-PHENYLMENTHYL CHLOROACETATE(71804-27-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 71804-27-8(Hazardous Substances Data)

Usage

Uses

(1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate may be used in the synthesis of (-)-8-phenyl-menthol, (+)-8-phenylmenthyl isocyanoacetate and (+)-cularine.

InChI:InChI=1/C18H25ClO2/c1-13-9-10-15(16(11-13)21-17(20)12-19)18(2,3)14-7-5-4-6-8-14/h4-8,13,15-16H,9-12H2,1-3H3/t13-,15-,16-/m1/s1

Upstream product

• 79-04-9 chloroacetyl chloride 
• 89-82-7 pulegone 
• 100-58-3 phenylmagnesium bromide 
• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 57707-91-2 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol 
• 152481-90-8 (1R,2S,5R)-(+)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl dichloroacetate 
• 65253-04-5 (-)-8-phenylmenthol 
• 134256-18-1 5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexanol 
• 79-11-8 chloroacetic acid 

Downstream Products

• 155795-48-5 (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 
• 438620-31-6 (1R,3R,4S)-8-phenylmenthyl 1-indoleacetate 
• 203253-78-5 (-)-8-Phenylmenthyl α-(cyclohex-1-enyl)-α-hydroxyacetate 

Relevant articles and documents

Samarium(II) Iodide-Mediated Synthesis of Chlorohydrins

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Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched α-Hydroxy-α-perfluoroalkyl Esters

This study has led to the development of a novel, highly efficient, 1,2-perfluoro-alkyl/-aryl migration process in reactions of hydrate of 1-perfluoro-alkyl/-aryl-1,2-diketones with alcohols, which are promoted by a Zn(II)/bisoxazoline and form α-perfluoro-alkyl/-aryl-substituted α-hydroxy esters. With (-)-8-phenylmenthol as the alcohol, the corresponding menthol esters are generated in high yields with excellent levels of diastereoselectivity. The mechanistic studies show that the benzilic ester-type rearrangement reaction takes place via an unusual 1,2-migration of electron-deficient trifluoromethyl group rather than the phenyl group. The overall process serves as a novel, efficient, and simple approach for the synthesis of highly enantioenriched, biologically relevant α-hydroxy-α-perfluoroalkyl carboxylic acid derivatives.

Asymmetric induction in Darzens condensation by means of (-)-8-phenylmenthyl and (-)-menthyl auxiliaries

Asymmetric Darzens condensation of benzaldehyde and various ketones has been investigated. The condensation of acetophenone, propiophenone and symmetric ketones with (-)-8-phenylmenthyl halogenoacetates 3a,b afforded the corresponding glycidic esters cis-12, cis-13 and 15-19 in 77-96% de, respectively, as the major products. Aza-Darzens condensation between N-benzylideneaniline and 3a occurred to give the trans-aziridine 21 as the major isomer in >85% de. The stereochemistry of the major diastereoisomers of cis-12 and 18 was confirmed by their conversion into the known optically active diols 22 and 24. The configuration of the major product of cis-12 was determined to be 2R,3R and that of 18 to be 2R. The geometric and disastereofacial selectivities were understandable in terms of the open-chain or non-chelated antiperiplanar transition state model in the initial aldol-type reaction.