Sulfuric Acid → HCID 58240635, compound

Participants

Reaction Steps

Concentrated sulphuric acid (0.7 ml) was added to a stirred solution of isolongifolan-8-one (1, 30.0 g, 90% pure, 0.12 mol) in isopropenyl acetate (150 ml). The reaction mixture was heated at reflux for 45 minutes, basified with saturated aqueous solution of sodium bicarbonate (200 ml) and extracted with MTBE (200 ml). The filtrate was washed with water (2×200 ml), dried (Na2SO4), concentrated in vacuo and distilled under reduced pressure to give (at 95° C./<1 mbar) a mixture of 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undec-4-en-5-yl acetate and 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undec-5-en-5-yl acetate (2a+2b: 70+25.5%, 30.5 g, 90% yield, pale yellow oil).

Provenance & Evidence