Water → 2-(4-Methoxyphenyl)propanenitrile
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]=1Participants
4
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
- temperatureThe reaction mixture is cooled
- extractionextracted with ether
- extractionThe ether extract
- washis washed
- dry with materialdried over Na2SO4
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- customyielding a liquid which
- distillationupon distillation
Sources & evidence
- ORD record
- ord-a6ee514441124d1b96644a5630120b04
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04588719
Reaction notes
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