Acetic Anhydride → Dimethyl 1,2,3,6-tetrahydro-4-acetyl-phthalate

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Reaction Steps

10 g dimethyl 1,2,3,6-tetrahydro-phthalate (II) was treated at -5° C. with 25 ml of acetic anhydride in the presence of 9 ml of tin tetrachloride. The reaction mixture was poured into iced water and extracted with diethyl ether. The organic phase was washed with a saturated aqueous solution of sodium bicarbonate and then with water, and was then evaporated to dryness under vacuum. The obtained oil was dissolved in benzene, treated with a methanolic solution of hydrogen chloride. The solution was evaporated to dryness and the residue was purified by chromatography on column of silica gel to give 9 g of the title compound in 75% overall yield. mass spectrum: m/z 240 (M+.)

Provenance & Evidence