Sulfuric Acid → 1-(Oxan-4-yl)propan-1-one

Participants

Reaction Steps

In a flask made of glass having an inner volume of 10 ml and equipped with a stirring device, a thermometer, a dropping funnel and a reflux condenser were charged 4.8 g (24 mmol) of 4-propionyl-4-methoxycarbonyltetrahydropyran synthesized in Example 2, 30 ml of water and 9.0 g of conc. sulfuric acid, and the mixture was reacted at 100° C. for 10 hours with stirring. After completion of the reaction, to the resulting reaction mixture was added 16.5 g of 50% by weight aqueous sodium hydroxide solution to adjust a pH of the mixture to 4.0. Said reaction mixture was extracted three times with 50 ml of ethyl acetate, and the organic layer was separated and concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography (Eluent; hexane/ethyl acetate=3/1 (volume ratio)) to give 2.58 g (Isolation yield: 76%) of 4-propionyltetrahydropyran as a pale yellow liquid.

Provenance & Evidence