Formic Acid → Methyl 2-(3-formylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of (3-cyanophenyl)acetic acid methyl ester 47 (0.86 g, 4.9 mmol) in 88% formic acid (6 mL) is combined with Raney nickel alloy (0.48 g) and heated to reflux for 24 hours at 110° C. After cooling to room temperature, the alloy is removed by filtration over Celite. The filtrate is concentrated to ˜10% of the original volume and diluted with EtOAc (50 mL) and washed three times with water (20 mL). The organic layer is dried (MgSO4), filtered and concentrated to afford crude product, which is purified by silica gel chromatography using an EtOAc/hexane gradient to give (3-formylphenyl)-acetic acid methyl ester 48 as an oil: 1H-NMR (400 MHz, CDCl3) δ=9.97 (s, 1H), 7.40-7.52 (m, 4H), 3.68 (s, 3H), 3.67 (s, 2H). MS calculated for C10H11O3 (M+H+) 179.1, found 179.1.

Provenance & Evidence