Benzoic Acid → cyanomethyl benzoate

Temperature

0 °C

To a suspension of 50.0 g (0.41 mol) benzoic acid in 150 mL N,N-dimethylformamide 70.0 g (0.50 mol) potassium carbonate was added and the mixture was stirred until the evolution of gas has ceased. The reaction mixture was cooled to 0° C. and a solution of 29.0 mL (0.41 mol) bromoacetonitrile in 50 mL N,N-dimethylformamide was added dropwise. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was dissolved in 500 mL ethyl acetate. It was washed with water (3×150 mL), saturated aqueous sodium hydrogencarbonate (150 mL) and brine. The organic layer was separated and dried over anhydrous sodium sulfate. The drying agent was filtered off and the solvent was evaporated. The resulting crude product was purified by column chromatography (hexane-ethyl acetate 9:1 to 4:1) to yield cyanomethyl benzoate 62.6 g (95%). 1H-NMR (400 MHz; DMSO-d6): 7.98 (m, 2H), 7.69 (m, 1H), 7.54 (m, 2H), 5.20 (s, 2H); GCMS for C9H7NO2: 161 (MH+).

1. additionwas added
2. stirringThe reaction mixture was stirred overnight at room temperature
3. customThe solvent was evaporated
4. dissolutionthe residue was dissolved in 500 mL ethyl acetate
5. washIt was washed with water (3×150 mL), saturated aqueous sodium hydrogencarbonate (150 mL) and brine
6. customThe organic layer was separated
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe drying agent was filtered off
9. customthe solvent was evaporated
10. customThe resulting crude product was purified by column chromatography (hexane-ethyl acetate 9:1 to 4:1)

ORD record

ord-405385960754483e989b1639330168e0

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576074B2