Methanol → Benzyl 4-formylbenzoate

Participants

Reaction Steps

4-Formyl-benzoic acid (2.0 g, 13.3 mmol) was made 0.2 M in 10:1 MeOH:Water and stirred. The stirring slurry was adjusted to pH=8 with 20% aq Cs2CO3. The resulting homogenous solution was stirred at ambient temperature for 20 mins then concentrated to dryness in vacuo. The residue was dried under high vacuum then treated with benzyl bromide (3.4 g, 20.0 mmol) 0.5 M in DMF. The slurry was stirred under nitrogen at ambient temperature for 18 hours. The reaction mixture was diluted with ½ saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was separated and again washed with ½ saturated aqueous sodium bicarbonate, then washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by MPLC (5-45% EtOAc in Hexanes) to afford the title compound: MS: cal'd 241 (MH+), exp 241 (MH+)

Provenance & Evidence