70985-58-9

Basic information

• Product Name: (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid
• Synonyms: (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid
• CAS NO: 70985-58-9
• Molecular Weight: 184.279
• Mol File: 70985-58-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid(70985-58-9)
• EPA Substance Registry System: (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid(70985-58-9)

Safety Data

• Hazardous Substances Data: 70985-58-9(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 80482-64-0 (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde 
• 485843-44-5 menthyl 3-carboxaldehyde 
• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 180978-26-1 (1S,2S,5R)-1-cyano-2-isopropyl-5-methylcyclohexane 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 2216-51-5 (-)-menthol 

Downstream Products

• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 1207722-22-2 (1S,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanecarbonyl Chloride 
• 1207722-11-9 (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide 

Relevant articles and documents

Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles

Menthyl Grignard reagent 1 from either menthyl chloride (2) or neomenthyl chloride (3) consists of menthylmagnesium chloride (1a), neomenthylmagnesium chloride (1b), trans-p-menthane (4), 2-menthene (8), 3-menthene (9), and Wurtz coupling products including symmetrical bimenthyl 13. The diastereomeric ratio 1a/1b was determined in situ by 13C NMR or after D2O quenching by 2H NMR analysis. Hydrolysis of the C-Mg bond proceeds with retention of configuration at C-1. The kinetic ratio 1a/1b from Grignard reagent generation (dr 59:41 at 50 °C in THF) is close to the thermodynamic ratio (56:44 at 50 °C in THF). Carboxylation of 1 at -78 °C separates diastereomers 1a/b to give the anion of menthanecarboxylic acid (19) from 1a, which combines with unreactive 1b to give neomenthylmagnesium menthanecarboxylate (1bI). The kinetics of epimerization for the menthyl/neomenthylmagnesium system was analyzed (ΔH? = 98.5 kJ/mol, ΔS? = -113 J/mol·K for 1bI → 1aI). Reactions of 1 with phosphorus electrophiles proceed stereoconvergently at C-1 of 1a/b to give predominantly menthyl-configured substitution products: PCl3 and 2 equiv of 1 give Men2PCl (6), which hydrolyzes to dimenthylphosphine P-oxide (7), whereas Ph2PCl with 1 equiv of 1 gave P-menthyldiphenylphosphine oxide (27) after workup in air.

Process for making neo-enriched p-menthane compounds

A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

INTERCONVERSION BETWEEN ISOMERIC P-MENTHANE-3-CARBOXYLIC ACIDS

A process for interconversion between WS-1 and neo-WS-1 by heating to a temperature in a range of from 60 degrees Celsius to 250 degrees Celsius. The heating can be done in the presence of an acid catalyst. Starting from practically pure (=98%) WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) neo-WS-1 can be obtained. Starting from practically pure (=98%) neo-WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) WS-1 can be obtained.