Benzoic acid, 3-(hydroxymethyl)-, 1,1-dimethylethyl ester synthesis

Yield:215522-96-6 99%

Reaction Conditions:

Stage #1: tert-butyl 3-formylbenzoatewith sodium tetrahydroborate in tetrahydrofuran;methanol at 0; for 1 h;
Stage #2: with ammonium chloride in tetrahydrofuran;methanol;water;

Steps:

B187.1

Sodium tetrahydroboride (746 mg, 17.7 mmol) was added with ice cooling to a THF (10 mL)-MeOH (40 mL) solution of tert-butyl 3-formylbenzoate (1.83 g, 8.87 mmol), and stirred for 1 hour with ice cooling. Saturated aqueous ammonium chloride solution was added to complete the reaction. The reaction solution was concentrated under reduced pressure, and extracted twice with ethyl acetate. The organic layer was washed successively with water and saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent was filtered out, and the filtrate was concentrated under reduced pressure to obtain tert-butyl 3-(hydroxymethyl)benzoate (1.83 g, 99%) as a colorless oil. ¹H-NMR (300MHz, CDCl₃); δ1.62 (s, 9H), 4.75 (s, 2H), 7.39-7.44 (t, J=7.8Hz, 1H), 7.53-7.56 (d, J=7.5Hz, 1H), 7.91-7.93 (d, J=7.8Hz, 1H), 7.97 (s, 1H)

References:

EP1849465,2007,A1 Location in patent:Page/Page column 142