Tetrahydrofuran → 3-Methoxypropiophenone

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methoxyphenylmagnesium bromide in tetrahydrofuran (500 ml) was prepared from 3-methoxybromobenzene (187 g) and magnesium turnings (24 g) and was added over 1.5 hours to a mixture of propionic anhydride (260 g) and diethyl ether (500 ml) which had been cooled to -70° C. A saturated aqueous solution of ammonium chloride (500 ml) was added and the mixture was allowed to warm to ambient temperature. The organic layer was separated and washed in turn with a dilute aqueous sodium hydroxide solution and with a saturated aqueous sodium chloride solution. The organic layer was dried (Na2SO4) and evaporated to give 3-methoxypropiophenone as a yellow oil (160 g).

Provenance & Evidence