Hydrochloric Acid → 3-Benzyloxetane-3-carboxylic acid

Participants

Reaction Steps

Jones reagent, (130 mL of a 2.3 M solution) previously prepared by adding hydrochloric acid (46 mL) to water (150 mL) followed by chromium (VI) oxide (55.5 g), was added dropwise to a solution of (3-benzyloxetan-3-yl)methanol (40 g, 0.2 mol) in acetone (600 mL). The reaction mixture was stirred at room temperature for 5 h. Isopropanol (18 g) was added and the mixture was extracted with ether (4 L), washed with NaH2PO4 (1M in water, 200 mL) and sodium chloride (1 M in water, 200 mL). The organics were dried over sodium sulfate, filtered and concentrated. The residue was triturated with ether (100 mL) to afford the title compound (37 g, 0.2 mol, 85%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 3.22 (s, 2H), 4.49-4.51 (d, 2H), 4.65-4.67 (d, 2H), 7.12-7.27 (m, 5H), 12.85 (s, 1H).

Provenance & Evidence