Benzyl Bromide → 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

Participants

Reaction Steps

6-Hydroxy-1-tetralone (10 g, 61.65 mmol), benzyl bromide (8.1 ml, 67.82 mmol) and K2CO3 (21.3 g, 154 mmol) in acetone (40 ml) were heated under reflux 2.5 hr. Following filtration and evaporation of the solvent the crude material was acidified to pHl with 1N HCl and partioned between H2O (150 ml) and EtOAc (150 ml). The aqueous phase was further extracted with EtOAc (100 ml) and the extracts dried (Na2SO4) filtered and evaporated to afford 6-benzyloxy-1-tetralone as an orange solid (12.37 g, 49.3 mmol, 80%) Mp. 97-100° C., MS m/e=252.1 (M+).

Provenance & Evidence