Hydrochloric Acid → Cyclopropyl 3-methylphenyl ketone

Participants

Reaction Steps

m-Bromotoluene (34.2 g) in dry ether (120 ml) was added dropwise to magnesium turnings (4.8 g) in dry ether (100 ml). The heat of reaction maintained the mixture to boiling under reflux during the addition and the mixture was heated under reflux for a further hour. The mixture was cooled to 0°, dry cadmium chloride (19.6 g) was added and the temperature allowed to rise to 20° C. After 1 hour, cyclopropanecarbonyl chloride (20.8 g) in dry ether (50 ml) was added dropwise and the mixture was heated under reflux for 4 hours, cooled to 0° and treated with 2 N hydrochloric acid. The ether layer was separated, washed with aqueous sodium bicarbonate (3× 100 ml., 8%) and with water, dried over magnesium sulphate, filtered and evaporated. The residue was distilled under reduced pressure and the fraction b.p. 86°-90°/0.4 mm was collected.

Provenance & Evidence