p-Tolylacetic acid → Chloromethyl p-Methylphenylacetate

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 4-methylphenylacetic acid (2.27 g, 15.15 mmol), sodium hydrogen carbonate (5.09 g, 60.6 mmol) and tetra-n-butylammonium hydrogen sulfate (0.51 g, 1.52 mmol) in water-dichloromethane (62.5 mL, 1:1 v/v) and chloromethylchlorosulfate (2.50 g, 15.15 mmol) in dichloromethane (7.5 mL), at room temperature for 18 h. Purification by flash chromatography (hexane/ethyl acetate 9:1) afforded 322 as a colourless oil (2.42 g, 12.18 mmol, 80%).

Provenance & Evidence