Hydrochloric Acid → 7-carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

Participants

Reaction Steps

A mixture of 7-acetylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (86 mg), 2.4 ml of aqueous solution of sodium hypochlorite and a small amount of surface active agent (polyoxyethylene octyl phenyl ether) was stirred at 60° C. for 2 hours. After cooling, the reaction mixture was diluted with water, and to the mixture was added 40% aqueous solution of sodium hydrogen sulfite. The reaction mixture was made acidic with hydrochloric acid, and resulting crystals were extracted with ethyl acetate. After washing with water and drying, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give colorless needles of 7-carboxyspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one. m.p. 259°-262° C. (decomp). Sublime at 183° C.

Provenance & Evidence