Phenol, 3-(1,1-dimethylethyl)- → 4-tert-Butyl-2-hydroxybenzaldehyde

Participants

Reaction Steps

A stirred, cooled (ice bath) solution of 3-tert-butyl phenol (1.5 g, 10 mmol) in anhydrous dichloromethane was treated with titanium tetrachloride (1.86 mL, 17 mmol) followed by . . . ,-dichloromethyl ether (0.9 mL, 20 mmol). The reaction was allowed to warm to ambient temperature over 1 h, quenched cautiously with ice and water and extracted with dichloromethane. The organic extract was washed with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column_chromatography using 2-2.5% ethyl acetate in hexane as the eluent to afford the title compound (1.37 g, 77%). 1H NMR (300 MHz, CDCl3): δ 11.02(s, 1H), 9.81(s, 1H), 7.45(d, J=8.2 Hz, 1H), 7.03(dd, J=8.2, 1.7 Hz, 1H), 6.99(d, J=1.7 Hz, 1H), 1.31(s, 9H).

Provenance & Evidence