2-(4-Chlorophenyl)-2-methylpropionic acid → 2-(4-Chlorophenyl)-2-methylpropanol

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Reaction Steps

The 2-(4-chlorophenyl)-2-methyl-propionic acid (6.10 g, 30.7 mmol) was dissolved in 120 mL of dry THF at room temperature. A 70% w/w solution of Red-Al (28.25 mL, 0.101 mol) was added dropwise via syringe over 5 minutes (vigorous bubbling). The mixture was heated to reflux for three hours. The solution was cooled to 0 C and carefully quenched with the addition of saturated sodium tartrate solution (100 mL, violent hydrogen evolution) and 100 mL of water. The aqueous mixture was extracted with ethyl acetate, and the combined organic was washed with diluted NaHCO3 solution, then brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford 2-(4-chlorophenyl)-2-methyl-propan-1-ol as a colorless oil (5.70 g, 99%). The material was used without purification. 1H NMR (CDCl3, 400 MHz) δ 7.32 (s, 5H), 3.62 (d, J=4.4 Hz, 2H), 1.33 (s, 6H), 1.23 (t, J=4.4 Hz, 1H).

Provenance & Evidence