Water → 2-(4-Methoxyphenyl)propanenitrile

HRID 980795Notes

Reaction equation

HRID 980795 reaction equation
C([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C(O)=O)#N.O.[CH3:17][N:18](C=O)C>>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([CH3:3])[C:17]#[N:18])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 137111482-Cyano-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 122976702-(4-Methoxyphenyl)propanenitrile

Procedure

A stirred solution of α-cyano-β-(4-methoxyphenyl)propionic acid (127.3 g) in DMF (280 ml) is heated to 150° C. for 5 hours. The reaction mixture is cooled, poured into a liter of water and extracted with ether. The ether extract is washed, dried over Na2SO4, filtered and the filtrate evaporated in vacuo yielding a liquid which upon distillation yields the decarboxylated product as a clear liquid, B.P. 115° C. (1 mm).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customyielding a liquid which
  9. distillationupon distillation

Sources & evidence

ORD record
ord-895b128707814f9eab1008b25aa7bf73
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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