Nitrobenzene → Propiovanillone

Participants

Reaction Conditions

Reaction Steps

Powdered anhydrous aluminum chloride (3.0 g, 22.5 mmol) was dissolved in anhydrous nitrobenzene (10 mL) at 100° C. The solution was cooled and 2-methoxyphenyl propionate (2.0 g, 11.1 mmol) was added rapidly. The reaction mixture was heated at 60° C. for 1.5 h and cooled, 3 N NaOH was added, and the mixture was stirred for 15 min. The suspension was filtered off, washed with water. The filtrate was then washed with CH2Cl2 twice, acidified with 3 N HCl, extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography (petroleum ether/EtOAc=10/1 to 5/1) to give the desired product (874 mg, 44% yield) as a yellow oil.

Provenance & Evidence