Benzyl Bromide → Methyl 2-(benzyloxy)acetate

To a stirred solution of methyl glycolate (2 g, 22.2 mmol) in anhydrous diethyl ether (100 mL), at room temperature, under a nitrogen atmosphere, was added silver(I)oxide (10.3 g, 44.4 mmol). The suspension was stirred for 15 minutes and benzyl bromide (4.5 g, 26.3 mmol) was added. The mixture was stirred at the same temperature for 24 h and the insoluble materials were removed by filtration through a short pad of celite. The filtrate was concentrated under reduced pressure and the crude product chromatographed over a column of silica gel, eluting with 20% diethyl ether-petroleum ether to give 70, as a colorless liquid in 70% yield (2.8 g).

1. stirringThe mixture was stirred at the same temperature for 24 h
2. customthe insoluble materials were removed by filtration through a short pad of celite
3. concentrationThe filtrate was concentrated under reduced pressure
4. customthe crude product chromatographed over a column of silica gel
5. washeluting with 20% diethyl ether-petroleum ether

ORD record

ord-ef295e0bde284afe8d9ff0864129be02

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102622B2