Benzyl Bromide → 2-(Benzyloxy)-3-(tert-butyl)benzaldehyde

Participants

Reaction Steps

A suspension of 3-tert-butyl-2-hydroxybenzaldehyde (11.3 g, 63.5 mmol, 1.0 equiv), benzyl bromide (10.8 g, 7.5 mL, 63.5 mmol, 1.0 equiv), powdered K2CO3 (17.5 g, 127 mmol, 2.0 equiv) and MeCN (300 mL) was refluxed for 4 hr. The pale green suspension was cooled to room temperature, filtered, washing the solids with EtOAc (150 mL). The filtrate was concentrated under reduced pressure to give a pale green oil. The crude product was chromatographed on silica gel (175 g) packed in heptanes (loaded as a solution in heptanes). The column was eluted with heptanes (1 L), 2% MTBE/heptanes (1 L) and 3% MTBE/heptanes (1.5 L). Product fractions were concentrated under reduced pressure to give 14.6 g (86%) of 21 as a yellow oil.

Provenance & Evidence