Acetic Anhydride → HCID 54305885, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of acetic anhydride (90 mL), 4-(methylthio)benzaldehyde (13.17 g, 82.2 mmol), 2-(2-thienyl)acetic acid (12.09 g, 83.3 mmol), and triethylamine (8.60 g, 85 mmol) was heated to reflux for 4 hours. The reaction was cooled to 85° C., and water (80 mL) was added through an addition funnel. A brown solid was isolated by filtration and air dried to afford the propenoic acid (8.48 g, 37%): mp 201°-206° C. 1H NMR (DMSO-d6) 300 MHz 12.80 (br s, 1H), 7.77 (s,1H), 7.60 (d, J=5.2 Hz, 1H), 7.09 (m, 5H), 6.92 (d, J=3.3 Hz, 1H), 2.42 (s, 3H). 13C NMR (DMSO-d6) 168.24, 141.60, 141.30, 136.84, 131.08, 130.86, 128.46, 127.86, 125.51, 125.28, 14.52. Mass spectrum: M+H=277.

Provenance & Evidence