Sulfuric Acid → 1-(Spiro[4.5]dec-6-en-6-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-ethynylspiro[4.5]dec-6-ene (120 g, 0.748 mol) and sulfuric acid (11.6 g) in acetic acid (500 ml) was heated for 2 h at 75° C., poured into ice, treated with 2N aqueous NaOH (10 ml) and extracted twice with MTBE (150 ml). The combined organic phases were treated with 2N aqueous NaOH (pH>7), washed with water (400 ml), with a saturated aqueous solution of NaCl (400 ml), dried (MgSO4), and concentrated. Short-path Vigreux-distillation (0.08 mbar, head temperature: 85-90° C.) of the crude product (125 g) gave 1-(spiro[4.5]dec-6-en-6-yl)ethanone (62 g, 46%).

Provenance & Evidence