3-Hydroxybenzaldehyde → 3-(3-(Benzyloxy)propoxy)benzaldehyde

Participants

Reaction Steps

To a 3-L reaction vessel was charged and stirred cesium carbonate (209.6 g), 3-hydroxybenzaldehyde (67.6 g), dimethylformamide (DMF, 250 mL) and 3-bromopropyl phenylmethyl ether (113.4 g) at ambient temperature for ˜18 h. Water (567 mL) was added followed by tert-butyl methyl ether (907 mL). The bottom aqueous layer was separated and the organic layer washed with 1N sodium hydroxide (2×567 mL) and water (1×567 mL). The organic solution was concentrated to a minimum after which ethanol (200 proof, 907 mL) was added and the solution concentrated to a minimum and filtered though a 1-μm filter.

Provenance & Evidence