Hydrochloric Acid → 3-(2-Thenoyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

Anhydrous aluminium chloride (15.8 g, 0.12 mol) was added to a solution of succinic anhydride (11.9 g, 0.12 mol) in dry CH2Cl2 (50 MI) and the reaction mixture was cooled to 0° C. A solution of thiophene (10.0 g, 0.12 mol) in CH2Cl2 (50 MI) was then added dropwise maintaining the same temperature. The reaction mixture was allowed to warm up to room temperature and stirred for 8 h. The mixture was then cooled to 0° C. and the Ph was adjusted to ˜3 using 6N HCl. The organic product was extracted with CH2Cl2. The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% MeOH in CH2Cl2), to get 4-oxo-4-(thiophen-2-yl)butanoic acid (8.3 g, yield 38%). 1H NMR (400 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.00-7.98 (m, 2H), 7.26-7.23 (m, 1H), 3.21-3.18 (m, 2H), 2.58-2.55 (m, 2H). MS (ESI) m/z: Calculated for C8H8O3S: 184.02. found: 184.9 (M+H)+

Provenance & Evidence