Water → HCID 12363892, compound

Participants

Reaction Steps

A mixture of hydroquinone monobenzylether (1.7 g, 8.5 mmol) and tetramethylammoniumchloride (0.19 g, 1.7 mmol) in (S)-epichlorohydrine (2.0 ml, 25.5 mmol) was stirred at room temperature for 4 days. H2O (30 ml) and CH2Cl2 (50 ml) were added and the organic phase was separated. The water phase was extracted two times with CH2Cl2. The organic phases were then pooled, dried with Na2SO4 and the solvent evaporated. The residue was chromatographed over silica gel (hexane-Et2O, 3:1) to give (R)-{[4-(Phenylmethoxy)phenoxy]methyl}-oxirane (1.1 g, 50%) as a colorless solid, m.p. 70°-73° C., [α]D20 =-8.1° (c=1.0, methanol) and MS: m/e=256 (M+).

Provenance & Evidence