Benzene → 2-(4-Methoxyphenyl)-2-methylpropanal

Participants

Reaction Conditions

Reaction Steps

Step A Under Argon, a mixture of NaOH (2.8 g, 70 mmol), tetrabutylammonium iodide (0.6 g, 1.6 mmol) in benzene (8 mL) and H2O (2.8 mL) was heated at 70° C. to form a homogeneous mixture. A mixture of 4-methoxybenzyl chloride (Aldrich) (10 g, 64 mmol) and isobutyraldehyde (5.76 g, 80 mmol) in benzene (22 mL) was added dropwise. The resulting reaction mixture was heated at 70° C. for 3 h. The mixture was cooled, extracted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:30) to give 2-(4-methoxy-phenyl)-2-methyl-propionaldehyde as a colorless oil (4.1 g, 33%).

Provenance & Evidence