Hydroquinone → 1,4-Bis-methoxymethoxy-benzene

Participants

Reaction Steps

Stir a suspension of sodium hydride (60% in mineral oil, 3.81 g, 95.45 mmol) in anhydrous DMF (50 mL) under nitrogen atmosphere at 0° C. and add a solution of hydroquinone (5.00 g, 45.45 mmol) in anhydrous DMF (50 mL) dropwise. Add to this suspension methoxymethyl chloride (7.2 mL, 95.45 mmol) dropwise with additional gas evolution noted. Allow the reaction to warm to ambient temperature and stir for one hour. Quench the reaction with water and add diethyl ether. Wash the organic layer with 1N sodium hydroxide and brine. Dry the organic layer over sodium sulfate, concentrate in vacuo, and flash chromatograph with 20% ethyl acetate/hexane to yield 1,4-bis-methoxymethoxy-benzene 6 (5.64 g, 63%) as a clear oil. 1H NMR (CDCl3): 6.97 (s, 4H), 5.11 (s, 4H), 3.47 (s, 6H).

Provenance & Evidence