Isobutyric Acid → 2,2-Dimethyl-3-phenylpropanoic acid

Participants

Reaction Steps

To a solution of diisopropylamine (48.91 g, 483 mmol) in THF (100 mL) under nitrogen at 0° C. was added a solution of 2.5M n-butyllithium in hexane (179 mL, 447.5 mmol.) followed by the dropwise addition of isobutyric acid (15.77 grams, 179 mmols). The reaction mixture was stirred at room temperature for 1.5 hours, then cooled to −15° C. Benzyl chloride (22.66 g, 179 mmol) was added dropwise while maintaining the temperature below −5° C., and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between Et2O and water. The aqueous layer was acidified by the addition of concentrated HCl (36%, 50 mL), and extracted with Et2O (4×150 mL), The organic layer was dried over MgSO4 and concentrated to afford the title compound (21.36 g) as a colorless liquid. LC-MS (ES) m/z=177 [M−H]−.

Provenance & Evidence