Water → 2,4,6-Trichlorobenzyl alcohol

Participants

Reaction Steps

A solution of lithium aluminium hydride (1M in THF, 18 mmol, 18 ml) was added slowly to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol) in THF (70 ml) at 0°. After 1 h water (685 μl) was added, followed by aqueous sodium hydroxide (3M, 685 μl) and more water (2.06 ml). The suspension was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a slightly yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°δH (CDCl3) 7.35 (2H, s, ArH), 4.91 (2H, br s, CH2CH) and 2.07 (1H, br s, CH); m/z (ES, 60V) 193 (M--OH).

Provenance & Evidence