Water → 1-Methoxy-3-(methoxymethoxy)benzene

To a solution of 3-(methyloxy)phenol (10.38 g, 84 mmol) in tetrahydrofurane (100 ml, SCRC) was added NaH (60% wt., 1.824 g, 76 mmol, Aldrich) portionwise under ice-cooling. The reaction mixture was stirred at room temperature for 1 hour and bromomethyl methyl ether (9.5 g, 76 mmol, SCRC) was then added. The resulting mixture was stirred at room temperature for 2 hours and water (50 ml) was added. The reaction mixture was extracted with ethyl acetate (2 times 50 ml, SCRC) and the combined organic layers were dried over sodium sulphate, evaporated. The residue was purified by column chromatography on silica gel (EtOAc: PE=1:100) to afford the title compound (10.2 g) as a colorless liquid.

1. temperaturecooling
2. stirringThe resulting mixture was stirred at room temperature for 2 hours
3. extractionThe reaction mixture was extracted with ethyl acetate (2 times 50 ml, SCRC)
4. dry with materialthe combined organic layers were dried over sodium sulphate
5. customevaporated
6. customThe residue was purified by column chromatography on silica gel (EtOAc: PE=1:100)

ORD record

ord-4636459a750d41aa994fc7d1bba7ef56

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133175B2