Chloride → HCID 837248, compound

Participants

Reaction Steps

To a mixture of 5-amino-2-methylphenol (30 g, 244 mmol), 10% NaOH (210 mL) and dichloromethane (120 mL) was added at 0° C. slowly isobuyryl chloride (25.5 mL, 244 mmol) in dichloromethane (50 mL). The mixture was stirred at room temperature overnight. The aqueous layer was separated and extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure to give 37.2 g of N-(3-hydroxy-4-methyl-phenyl)-isobutyramide (78%). 1H NMR (300 MHz, CDCl3 ppm): δ: 1.21 (d, J=7.03 Hz, 6 H), 2.17(s, 3 H), 2.53 (m, 1 H), 2.58 (s, 3 H), 6.81(dd, J=2.05 Hz, 7.91 Hz, 1H), 6.97 (d, J=7.91 Hz, 1H), 7.38 (d, J=2.05 Hz, 1 H), 8.14 (bs, 1 H), 8.58 (s, 1 H).

Provenance & Evidence