Water → 5-Fluoro-2-methylphenylacetonitrile

HRID 1164355Notes

Reaction equation

HRID 1164355 reaction equation
[C-:1]#[N:2].[Na+].O.Cl[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH3:14]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([CH3:14])=[C:7]([CH2:6][C:1]#[N:2])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 205117952-(Chloromethyl)-4-fluoro-1-methylbenzene

Product 1

HCID 27746255-Fluoro-2-methylphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred and refluxing mixture of 71 parts of sodium cyanide, 99 parts of ethanol and 85 parts of water is added dropwise a solution of 134 parts of 2-(chloromethyl)-4-fluoro-1-methylbenzene in 99 parts of ethanol. Upon completion, stirring is continued first for 6 hours at reflux and further overnight at room temperature. The ethanol is evaporated and the residue is taken up in 4-methyl-2-pentanone and water. The layers are separated and the aqueous phase is extracted three times with 4-methyl-2-pentanone. The combined organic phases are washed twice with water, dried, filtered and evaporated. The residue is distilled, yielding 98 parts of 5-fluoro-2-methylbenzeneacetonitrile; bp. 124°-128° C. at 10 mm. pressure.

Workup

  1. temperaturerefluxing
  2. stirringUpon completion, stirring
  3. customThe ethanol is evaporated
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted three times with 4-methyl-2-pentanone
  6. washThe combined organic phases are washed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue is distilled

Sources & evidence

ORD record
ord-b26319d057a441ac921d0da957646c3a
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

Loading…