Benzaldehyde → 2-Cyano-3-phenylprop-2-enoic acid

HRID 225155Notes

Reaction equation

HRID 225155 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

HCID 240BenzaldehydeHCID 8082PiperidineHCID 25917Isopropyl cyanoacetate

Product 1

HCID 705342-Cyano-3-phenylprop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. temperaturewas heated on a steam bath for 1 hour
  2. distillationThe acetic acid and unreacted benzaldehyde were distilled off, to 100° C./0.2 Torr
  3. extractionThe residue was extracted with hot hexane
  4. waitno residue was left
  5. temperatureThe solution was chilled
  6. customthe solid that formed
  7. 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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