Acetic Acid → Ethyl benzylidenecyanoacetate

HRID 1607387Notes

Reaction equation

HRID 1607387 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][CH2:15][CH3:16])=[O:13])#[N:10].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([C:9]#[N:10])=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 74845Ethyl benzylidenecyanoacetateYield 104.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2.55 g of benzaldehyde, 2.46 g of ethyl cyanoacetate, 0.3 ml of acetic acid and 0.3 ml of piperidine in 20 ml of dry benzene was heated under reflux for 16 hours while removing water formed during the reaction by using a molecular sieve. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 4.57 g of 2-cyano-3-phenylpropenoic acid ethyl ester as colorless crystals.

Workup

  1. temperatureunder reflux for 16 hours
  2. customwhile removing water
  3. customformed during the reaction
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e852ae90d1d9468e922bfe563e52f043
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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