Acetic Anhydride → HCID 15418433, compound

Participants

Reaction Steps

A mixture of cyclopropane-1,1-dicarboxylic acid (13.0 g, 0.10 mmol), cyclohexanone (10.8 g, 0.11 mol), acetic anhydride (11.2 g, 0.11 mol) and concentrated sulphuric acid (5 drops) was stirred at room temperature 0.5 h. The mixture soon became a wine-red solution which later darkened to purple. The reaction mixture was partitioned between water (100 ml) and ether (2×100 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), filtered and evaporated to leave a purple oil plus some solid material. This mixture was purified by column chromatography on silica [eluent=ether/hexane (4:1)] to give the title compound as colourless crystals (2.70 g, 13%), m.p. 134.5°-135° C.

Provenance & Evidence