Water → {3-[2-(2-Chloroacetamido)-2-methylpropyl]phenyl}acetic acid

Participants

Reaction Steps

Concentrated sulphuric acid (21 ml) was added dropwise to a solution of [3-(2-hydroxy-2-methylpropyl)-phenyl]-acetic acid (Preparation 49) (10.6 g, 51.0 mmol) and chloroacetonitrile (4.8 ml, 76.0 mmol) in glacial acetic acid (16 ml) at 0° C. The reaction was allowed to warm to room temperature and after 2 hours was poured onto iced water (500 ml). The aqueous was extracted with ethyl acetate (2×250 ml) and the combined organics washed with brine (50 ml), dried (sodium sulfate), and the solvent removed in vacuo to furnish the title compound as a golden oil (14.0 g). 1H NMR (400 MHz, CDCl3): δ=7.31-7.06 (4H, m), 6.19 (1H, bs), 3.95 (2H, s), 3.62 (2H, s), 3.02 (2H, s), 1.36 (6H, s) ppm. LRMS (electrospray): m/z [M−H]− 282/284.

Provenance & Evidence