Sodium Cyanide → 4-(Cyanomethyl)benzoic acid

Temperature

25 °C

A solution of 4-bromomethyl-benzoic acid (4.0 g, 18.6 mmol) in acetonitrile (186 mL) was treated with a solution of sodium cyanide (1.0 g, 20.4 mmol) and sodium hydroxide (0.74 g, 18.6 mmol) in water (24 mL). The reaction mixture was heated at reflux for 2 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The resulting solution was washed with chloroform (1×50 mL). The aqueous layer was acidified to pH=3 with a 1N aqueous hydrochloric acid solution. The aqueous layer was extracted with a solution of chloroform/methanol (9:1, 3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-cyanomethyl-benzoic acid (0.79 g, 26.3%) as a white solid: mp 193–195° C.; EI-HRMS m/e calcd for C9H7NO2 (M+) 161.0476, found 161.0483.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 2 h
3. concentrationconcentrated in vacuo
4. washThe resulting solution was washed with chloroform (1×50 mL)
5. extractionThe aqueous layer was extracted with a solution of chloroform/methanol (9:1, 3×100 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-1ad1621af5464faaada95cf33efc5f9e

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223868B2