Sodium Cyanide → Benzeneacetonitrile, ar,ar,ar-trichloro-

To a stirred solution of 1,3,5-trichloro-2-chloromethyl-benzene (12.85 g, 58.8 mmole) in ethanol (45 ml), NaCN (3.20, 67.0 mmole) solution in water (15 ml) was added at ambient temperature. The reaction mixture was refluxed for 4 hours to complete the reaction. Ethanol was evaporated and the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with EtOAc (3×100 ml). The combined organic layer was washed with brine (30 ml) and dried over sodium sulfate. Organic layer was concentrated under vacuum to give white solid. Crude product was purified by chromatography on silica-gel column to afford 9.0 g (75.0% of theory) of (2,4,6-trichloro-phenyl)-acetonitrile

1. temperatureThe reaction mixture was refluxed for 4 hours
2. customthe reaction
3. customEthanol was evaporated
4. additionthe reaction mixture was diluted with water (50 ml)
5. extractionThe aqueous layer was extracted with EtOAc (3×100 ml)
6. washThe combined organic layer was washed with brine (30 ml)
7. dry with materialdried over sodium sulfate
8. concentrationOrganic layer was concentrated under vacuum
9. customto give white solid
10. customCrude product was purified by chromatography on silica-gel column

ORD record

ord-e60c90e2c8054908a541acad3b624f31

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258169B2