Water → Methyl 2-(2-(benzyloxy)phenyl)acetate

Participants

Reaction Steps

Methyl 2-hydroxyphenylacetate (21.0 g) was dissolved in dry DMF (200 ml), and dry potassium carbonate (19.35 g) was added in one portion. Benzyl bromide (23.94 g) in dry DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature. After eighteen hours the mixture was poured into water (500 ml) and extracted with ether (2×400 ml). The extracts were washed with water (3×150 ml) and brine (100 ml), dried and filtered through silica gel (50 g; Merck 60), then concentrated under reduced pressure to afford a yellow oil. Distillation at 160° C. and 0.05 mmHg afforded methyl 2-benzyloxyphenylacetate as a clear, colourless oil (26.99 g; 83% yield), infrared maximum (film): 1730 cm-1 ; 1H nmr (CDCl3, 90 MHz): delta 3.60 (3H, s), 3.75 (2H, s), 4.10 (2H, s), 6.80-7.40 (9H, m) ppm.

Provenance & Evidence