Sulfuric Acid → Tert-butyl 4-((methoxycarbonyl)methyl)benzoate

Participants

Reaction Steps

To a solution of 4-(2-methoxy-2-oxoethyl)benzoic acid (0.87 g, 4.48 mmol) in methylene chloride (5 mL) was condensed isobutylene (approximately 20 mL) at −78° C. The solution was treated with 0.5 mL concentrated sulfuric acid and the solution was sealed in a stainless steel bomb and allowed to warm to ambient temperature for 6 hours. The solution was recooled to −78° C. and opened. The reaction was partitioned between 0.1M sodium hydroxide solution and diethyl ether. The organics were dried over sodium sulfate, filtered and evaporated. Purification by flash chromatography (0-35% ethyl acetate/hexanes) gave tert-butyl 4-(2-methoxy-2-oxoethyl)benzoate as a clear oil. 1H NMR (600 MHz, DMSO-d6) δ 7.81 (d, J=8.21 Hz, 2H), 7.35 (d, J=8.51 Hz, 2H), 3.75 (s, 2H), 3.56 (s, 3H), 1.51 (s, 9H); ESIMS calcd 251.1 (M++H), found 251.0 (M++H).

Provenance & Evidence