4-Methyloxybenzyl chloride → HCID 22035839, compound

Participants

Reaction Steps

A solution of 1.03 g (8.7 mmol) of 2,2-dimethyl-3-hydroxypropionic acid, 1.8 mL (12.9 mmol), of TEA and 1.3 mL (9.5 mmol) of para-methoxybenzyl chloride in 8 mL of DME was stirred at rt for 24 h. The mixture was partitioned between 200 mL Et2O and 100 mL of H2O. After separating layers, the organic phase was washed with 100 mL of 1 N NaHCO3, 100 mL of 2 N HCl, 2×100 mL of H2O, 100 mL of brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography using a gradient of 3:1 v/v to 3:2 v/v of hexanes/EtOAc as the eluant to afford the title compound: RF: 0.17 (4:1 v/v hexanes/EtOAc); 1H-NMR (500 MHz) δ 1.21 (s, 6H), 3.57 (s, 2H), 3.82 (s, 3H), 5.09 (s, 2H), 6.90 (d, J=8.8, 2H), 7.28 (d, J=8.8, 2H).

Provenance & Evidence