Phenylacetic Acid → Chloromethyl phenylacetate

Participants

Reaction Steps

A similar procedure (Harada, N. et al. Synth. Commun. 1995, 25, 767-772) to that described for the preparation of 43 was followed using phenylacetic acid (4.50 g, 31.2 mmol), sodium hydrogen carbonate (10.48 g, 124.8 mmol) and tetra-n-butylammonium hydrogen sulfate (1.06 g, 3.12 mmol) in water-dichloromethane (125 mL, 1:1 v/v) and chloromethylchlorosulfate (5.15 g, 31.2 mmol) in dichloromethane (15 mL), at room temperature for 18 h. Purification by flash chromatography (hexane/ethyl acetate 9:1) afforded 49 as a yellow oil (1.81 g, 9.82 mmol, 31%).

Provenance & Evidence