Methanol → HCID 69431017, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, thionyl chloride (11.3 g, 0.0948 mol) was slowly dropped into methanol (30 ml) at −5° C. over a period of 20 minutes. After 15 minutes, a solution of 3-methoxycyclohexylcarboxylic acid (5.0 g, 0.0316 mol, cis:trans=4:3) in methanol (30 ml) was added dropwise thereto over a period of 15 minutes. After 2.5 hours, the reaction solution was concentrated under reduced pressure, and the resulting residue was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution. The aqueous layer was re-extracted with ethyl acetate and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain methyl cis-3-methoxycyclohexane-carboxylate (3.0673 g, 56%) and methyl trans-3-methoxycyclohexanecarboxylate (1.5859 g, 29%).

Provenance & Evidence