Hydrochloric Acid → 2-Hydroxy-2-(3-nitrophenyl)acetonitrile

To a stirred solution of 3-nitrobenzaldehyde (5.0 g, 33.1 mmol) in dichloromethane (30 ml) at 0° C. was added trimethylsilyl cyanide (4.63 ml, 34.7 mmol). After stirring for 6 h at room temperature, zinc iodide (210 mg, 0.66 mmol) was added which caused the reaction mixture to warm and gently reflux. After 30 min, the reaction mixture was treated with hydrochloric acid (2M, 100 ml) and diethyl ether (150 ml) and stirred vigorously for 16 h. The phases were separated and the aqueous phase was further extracted with diethyl ether (3×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1 and then 1:1). This gave the title compound as a clear oil (5.0 g, 85%).

1. temperatureto warm
2. temperaturegently reflux
3. waitAfter 30 min
4. stirringstirred vigorously for 16 h
5. customThe phases were separated
6. extractionthe aqueous phase was further extracted with diethyl ether (3×100 ml)
7. dry with materialThe combined organic extracts were dried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto give a residue which
10. customwas purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1

ORD record

ord-146cfa4d975b4dc6aa984e7740070f23

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2