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-782d541837d74fd5acef9397e4c6fbfb

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422272B2