89036-22-6

Basic information

• Product Name: L-menthyl chloromethanesulphonate
• Synonyms: L-menthyl chloromethanesulphonate
• CAS NO: 89036-22-6
• Molecular Weight: 268.805
• Mol File: 89036-22-6.mol

Chemical Properties

• CAS DataBase Reference: L-menthyl chloromethanesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: L-menthyl chloromethanesulphonate(89036-22-6)
• EPA Substance Registry System: L-menthyl chloromethanesulphonate(89036-22-6)

Safety Data

• Hazardous Substances Data: 89036-22-6(Hazardous Substances Data)

Upstream product

• 3518-65-8 monochloromethanesulfonyl chloride 
• 2216-51-5 (-)-menthol 

Downstream Products

• 2216-52-6 Neomenthol 
• 5113-93-9 (1R)-trans-p-menth-2-ene 
• 2623-23-6 L-menthyl acetate 
• 107535-12-6 (1S,2S,4R)-2-azido-1-isopropyl-4-methylcyclohexane 

Relevant articles and documents

Chloromethanesulfonate as an efficient leaving group: Rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles

The chloromethanesulfonate (monochlate) served as an efficient leaving group for rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles. The treatment of the monochlate 16a with zinc acetate in dioxane at 90 °C effected migration of the 4α-methyl group to give alkene 17a. Upon similar treatment of the monochlates 22a, 25a, 28a, and 31a with zinc acetate, the carbon-carbon bonds antiperiplanar to the hydroxyl groups efficiently migrated to afford the alkenes 23a, 26a-c, 29a,b, and 32a, respectively. In the case of the diol 40, the monochlate was converted into the ketone 41 via a rearrangement-ring expansion. The reaction of the monochlates 44a, 47a, 49a, 52a, and 57a with sodium azide or lithium azide in N,N-dimethylformamide efficiently afforded the azides with inversion of the configuration. The introduction of a nitrile group to the sterically hindered alcohol 59 was performed in high yield by the reaction of the monochlate 60a with sodium cyanide.

Efficient method for inversion of secondary alcohols by reaction of chloromethanesulfonates with cesium acetate

Inversion of a variety of secondary alcohols using the (chloromethylsulfonyl)oxy group as a favorable leaving group with cesium acetate in the presence of 18-crown-6 has been performed to give the inverted acetates in high yields.

Asymmetric synthesis of α,β-epoxysulphonate esters (oxiranesulphonate esters)

The asymmetric phase-transfer-catalyzed Darzens condensation of aldehydes and ketones with the chiral reagent L-menthyl chloromethanesulphonate, using triethylbenzylammonium chloride (TEBA) as the phase-transfer catalyst to give α,β-epoxysulfonate esters (oxiranesulphonate esters) in 9-17 percent chiral induction, is described.The stereochemical course of the chiral induction is discussed.