Acetic Anhydride → HCID 68722435, compound

Participants

Reaction Conditions

Reaction Steps

A 81:14:3 mixture of 3-hydroxy-1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)butan-1-one, 3-hydroxy-1-(7-methylspiro[4.5]deca-6,8-dien-6-yl)butan-1-one, and 3-hydroxy-1-(7-methylenespiro[4.5]dec-8-en-6-yl)butan-1-one (0.2 g, 0.85 mmol), acetic anhydride (0.17 ml, 1.8 mmol) and sodium acetate (77 mg, 3.0 mmol) was stirred at 80° C. for 16 h, treated with sodium acetate (30 mg, 0.37 mmol), stirred at 80° C. for 2 h, cooled to 0° C., poured into cold saturated aqueous NaHCO3 (20 ml), and extracted three times with MTBE (10 ml). The combined organic phases were washed twice with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (30 g SiO2, hexane/MTBE 60:1) of the crude product (0.2 g) gave (E)-1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)but-2-en-1-one (0.139 g, 77%). Boiling point: 100° C. (0.07 mbar).

Provenance & Evidence