Methanol → Methyl 2-cyclopropyl-2-(4-chlorophenyl)acetate

Participants

Reaction Steps

A mixture of 10.0 grams (0.036 mole) of 2-[(4chlorophenyl)cyclopropylmethylene]-1,3-dithiane, 24.0 grams (0.086 mole) of mercury (II) chloride, and 5 mL of water in 50 mL of methanol was stirred at ambient temperature for 18 hours. The reaction mixture was heated at reflux for one hour, cooled, and then was diluted with diethyl ether. The mixture was filtered through diatomaceous earth and then was dried with magnesium sulfate. The mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure, yielding 5.9 grams of methyl 2-cyclopropyl-2-(4-chlorophenyl)acetate as an oil. The nmr spectrum was consistent with the proposed structure. The reaction was run again to produce an additional 7.1 grams of the acetate.

Provenance & Evidence