Acetic Acid → 53313-92-1

Temperature

15 °C

To a stirred suspension of KCN (5.04 g, 78 mmol) in methanol (20 mL) was added 3-chlorobenzaldehyde (7.0 g, 50 mmol) at 0° C. under nitrogen atmosphere. Then acetic acid (4.4 mL) was added dropwise at 0° C. After 30 minutes, the mixture was warmed to 15° C. and stirred for 5 hours. Then the reaction mixture was concentrated to dryness and extracted with ethyl acetate (200 mL). The organic solution was washed with water (3×25 mL), brine (25 mL), dried over anhydrous sodium sulfate and concentrated to dryness. The resulting residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:15) to afford (3-chloro-phenyl)-hydroxy-acetonitrile. (Yield 8.2 g, 97%). LC-MS: [M+Na]+ 190.

1. concentrationThen the reaction mixture was concentrated to dryness
2. extractionextracted with ethyl acetate (200 mL)
3. washThe organic solution was washed with water (3×25 mL), brine (25 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated to dryness
6. customThe resulting residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:15)

ORD record

ord-9176522c465b4c30a5f267ca286bafc7

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673905B2