Ethyl 2-(benzyloxymethyl)cyclopropanecarboxylate → 2-((Benzyloxy)methyl)cyclopropanecarboxylic acid

Participants

Reaction Steps

A solution of 0.23 mol of the compound obtained in Step 1 in 500 ml of ethanol, 230 ml of 1N sodium hydroxide solution and 5 ml of dimethyl sulphoxide is heated at reflux for 2 hours and is then concentrated. The residue is taken up in a mixture of water/ether. After conventional treatment, the combined organic phases are concentrated. Chromatography of the residue over silica gel (dichloromethane/tetrahydrofuran: 97/3) allows a cis/trans mixture of the products obtained to be isolated, some of the fractions of which have a preponderance of the cis isomer and some a preponderance of the trans isomer.

Provenance & Evidence