Benzaldehyde → 2-Cyano-3-phenylprop-2-enoic acid
Reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C:12]([O:14]C(C)C)=[O:13])#[N:10].N1CCCCC1>C(O)(=O)C>[C:9]([C:11](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([OH:14])=[O:13])#[N:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 95 g of benzaldehyde, 114.3 g of 7A, 1 g of piperidine and 200 ml of acetic acid was heated on a steam bath for 1 hour. The acetic acid and unreacted benzaldehyde were distilled off, to 100° C./0.2 Torr. The residue was extracted with hot hexane; no residue was left. The solution was chilled, and the solid that formed was recrystallized from methanol to give the 1-methylethyl ester of 2-cyano-3-phenyl-2-propenoic acid (7B), mp: 72°-73° C.
Workup
- temperaturewas heated on a steam bath for 1 hour
- distillationThe acetic acid and unreacted benzaldehyde were distilled off, to 100° C./0.2 Torr
- extractionThe residue was extracted with hot hexane
- waitno residue was left
- temperatureThe solution was chilled
- customthe solid that formed
- customwas recrystallized from methanol
Sources & evidence
- ORD record
- ord-8db14a2049184cc49281b1470652e865
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04235923
Reaction notes
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