Toluene → HCID 86602740, compound

Participants

Reaction Steps

To a reaction vessel were added 4-chloro-2-methoxyphenol 20.0 g (126 mmol), (S)-epichlorohydrin 23.3 g (252 mmol), benzyl trimethylammonium chloride 0.585 g (3.15 mmol), toluene 40 mL and water 40 mL. To this mixture was dropped an aqueous 24% NaOH solution 31.5 g (189 mmol) in an ice bath, and the mixture was stirred at room temperature for 36 hours. The water layer was removed and the organic layer was washed with an aqueous 5% HCl solution and a 5% NaCl solution successively. The organic layer was taken and the solvent was evaporated to give crude (R)-glycidyl 4-chloro-2-methoxyphenyl ether 22.1 g (yield 87%, chemical purity 93%) as a white solid.

Provenance & Evidence