4-Methyloxybenzyl chloride → HCID 71272208, compound

Participants

Reaction Steps

To a solution of 3-oxocyclobutanecarboxylic acid (20.0 g, 175.3 mmol) in DCM (500 mL) was added satd. aq. NaHCO3 (293 mL), tetrabutyl ammonium bromide (75.3 g, 227.9 mmol) and 4-methoxybenzyl chloride (33.0 g, 210.4 mmol) and the mixture was stirred at RT overnight. After the reaction was completed, the mixture was diluted with water and extracted with DCM (2×250 mL). The organic layer was washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (8:1) to afford 15.2 g (37%) of 4-methoxybenzyl 3-oxocyclobutanecarboxylate as an off-white solid.

Provenance & Evidence