Thioanisole → Ibuprofenal

Participants

Reaction Steps

To a solution of 38.0 g (0.2 mole) of 2-(4-isobutylphenyl)-1,2-epoxypropane in 130 ml of dichloromethane was added 3.43 g (0.036 mole) of anhydrous powdered (100 mesh, Tyler) magnesium chloride and 5.0 g (0.04 mole) of thioanisole and the mixture was stirred for 10 hours at room temperature. The reaction mixture was washed with dilute hydrochloric acid and then with aqueous sodium chloride several times until neutral, and subjected to distillation under atmospheric pressure to remove dichloromethane. The resulted residue was distilled under reduced pressure to afford 37.4 g of 2-(4-isobutylphenyl)propionaldehyde as colorless oil distilled at 127°-130° C. (8 mmHg). The yield is 98.5%

Provenance & Evidence