Chloromethyl Methyl Ether → 1-Methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene

Participants

Reaction Steps

To a solution of 2-(3-methoxyphenyl)-2-methyl-propan-1-ol (Intermediate 39, 900 mg, 4.99 mmol) in THF (15 mL) sodium hydride 60% dispersion in mineral oil (300 mg, 7.49 mmol) was added and the reaction mixture was stirred for 15 minutes at room temperature. Chloro(methoxy)methane (603.02 mg, 7.49 mmol) was added and the reaction mixture was heated to 55° C. and stirred overnight. The reaction was cooled to 0° C. and quenched with water (10 mL) (added dropwise) and extracted with EtOAc (30 mL). Organics were dried over Na2SO4, filtered and evaporated in vacuo to afford the title compound (525 mg) that was used in the next step without further purification.

Provenance & Evidence