4-Isobutylbenzoic acid → [4-(2-Methylpropyl)phenyl]methanol

Participants

Reaction Steps

A solution of lithium aluminum hydride (30 mL, 1M in THF, 30 mmol) was added dropwise to a solution of 4-isobutylbenzoic acid (5.34 g, 30 mmol) in THF (50 mL) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 1 h. The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N). The product was extracted into EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated to obtain (4-isobutyl-phenyl)-methanol which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ7.26 (d, 2H), 7.13 (d, 2H), 4.65 (s, 2H), 2.46 (d, 2H), 1.85 (m, 1H), 0.89 (d, 6H).

Provenance & Evidence