Guaiacol → 1-Methoxy-2-(methoxymethoxy)benzene

Participants

Reaction Steps

Potassium tert-butoxide (67.9 g, 605 mmol) was dissolved in a mixed solvent of DMF (500 mL) and THF (500 mL), then with cooling with ice, 2-methoxyphenol (68.28 g, 550 mmol) was dropwise added. This was stirred at room temperature for 2 hours, and then chloromethyl methyl ether (46 mL, 605 mmol) was added. After stirred for 5 hours at room temperature, aqueous saturated ammonium chloride solution was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, then dried with sodium sulfate, and concentrated. Purified by silica gel column chromatography, the intended compound (97.66 g, 100%) was obtained as a pale yellow oil.

Provenance & Evidence