Hydrochloric Acid → 1-(4,4-Dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one

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Reaction Steps

To a mixture of 16.3 g (122 mmol) of aluminum chloride, 11.77 g (10.7 mmol) of acetyl chloride and 110 ml of carbon disulfide was added, slowly, with stirring, 18.0 g (111 mmol) of 4,4-dimethylchroman, at 0 to 5° C. After the addition was complete, stirring was continued for 4 hours at 0° C. The mixture was then poured onto 200 ml of 6N hydrochloric acid and 200 g of ice. The resulting mixture was extracted with 500 ml of diethyl ether. The ether extract was dried (MgSO4) and evaporated in vacuo to give an oil, which was fractionally distilled, under reduced pressure, to give 6.99 g (31% yield) of the title compound, bp 110°-113° C. (0.03 mm Hg).

Provenance & Evidence