Benzene → HCID 53829222, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 30 g of (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylic acid chloride and 50 ml of benzene was added to a solution of 15 g of methanol, 15 g of pyridine and 200 ml of benzene and the mixture was stirred at 20° C. for 8 hours and was then poured into iced water. The decanted organic phase was washed with water, with a sodium bicarbonate solution, with water, with dilute hydrochloric acid and finally with water. The organic phase was dried and evaporated to dryness under reduced pressure at 45° C. The residue was chromatographed over silica gel and was eluted with an 8-2 petroleum ether (b.p.=60°-80° C.)-isopropyl ether mixture to recover the fraction with an Rf=0.5. The solvent was distilled off under reduced pressure at 45° C. and the residue was rectified under reduced pressure to obtain 23 g of methyl (1R,cis) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylate with a boiling point of 63°-64° C. at 0.1 mm Hg and a specific rotation of [α]D20 =+119° (c=1.5% in chloroform).

Provenance & Evidence