Dichloromethane → 2-(3-Chlorophenyl)oxirane

Participants

Reaction Conditions

Reaction Steps

Synthesis of (±)-1: The aqueous solution of trimethylsulfonium sulfate (20 mL, 1.05×10−1 mol) was added slowly to a two-phase mixture of 50% NaOH (100 mL), 3-chlorobenzaldehyde (7.03 g, 5.00×10−2 mol), tetrabutylammonium bromide (0.126 g, 3.91×10−4 mol), and CH2Cl2 (132 mL). The reaction was heated at 50° C. for 13 hours and then cooled to room temperature. The reaction was diluted carefully with brine (250 mL) and diethyl ether (350 mL), and then filtered to remove solids. The aqueous layer was extracted with diethyl ether (3×350 mL), and the combined organic layers were washed with brine (200 mL) and dried over Na2SO4, filtered, and concentrated in vacuo to afford a pale yellow liquid. Bulb-to-bulb distillation (70° C., 0.6 mm Hg) from CaH2 afforded 1 (7.12 g, 92%) as a colorless liquid. 1H NMR (CDCl3) δ 7.27 (m, 3H), 7.17 (m, 1H), 3.83 (dd, J=2.5, 4.1 Hz, 1H), 3.15 (dd, J=4.1, 5.5 Hz, 1H), 2.76 (dd, J=2.5, 5.5 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 139.9, 134.7, 129.9, 128.4, 125.6, 123.8, 51.8, 51.3; IR (thin film, cm−1) 3057, 2994, 2920, 1603, 1576, 1080; CIHRMS calcd for C8H7ClO (M+NH4)+=172.0529, found 172.0527.

Provenance & Evidence