Benzyl Alcohol → HCID 12555046, compound

Participants

Reaction Steps

3,4-Dihydroxy-3-cyclobutene-1,2-dione (2.0 g, 17 mmol), benzyl alcohol (5.0 mL, 5.2 g, 48 mmol), and p-toluenesulfonic acid monohydrate (170 mg, 0.9 mmol) were slurried in toluene (20 mL), and heated under reflux with a Dean-Stark trap for 3 days. The insoluble material was filtered off, and the filtrate was diluted with ether (100 mL), washed with 2× with saturated aqueous NaHCO3 solution and brine, dried over Na2 SO4, filtered and concentrated to a crude residue. The crude product was purified by chromatography eluting with 4:1 hexane-EtOAc to give the title compound (1.5 g, 29%) as an oil which slowly solidified on standing. MS (FAB+) m/e 312 (M+NH3 +H)+.

Provenance & Evidence