Ethyl 2-methyl-2-(4-methylphenyl)propanoate → 2,2-Dimethyl-2-(4-methylphenyl)ethanol

Participants

Reaction Steps

To a solution of 2-methyl-2-p-tolyl-propionic acid ethyl ester (510 mg, 2.47 mmol) in THF (10 mL) at 0° C. was added lithium aluminum hydride (1M in Et2O, 2.6 mL, 2.6 mmol). The reaction was stirred for 0.5 h and the reaction was quenched by consecutive addition of water (0.1 mL), 15% NaOH (0.1 mL), and water (0.3 mL). The reaction was diluted with EtOAc, dried (MgSO4), filtered and concentrated to yield 2-methyl-2-p-tolyl-propan-1-ol (405 mg). 1H NMR (400 MHz, CDCl3) δ 7.27 (d, 2H), 7.15 (d, 2H), 3.58 (s, 2H), 2.32 (s, 3H), 1.31 (s, 6H); MS 165 (M+1).

Provenance & Evidence