Acetic Acid → 80540-68-7

HRID 358121Notes

Reaction equation

HRID 358121 reaction equation
[C:1]1([CH3:9])[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:10]([CH2:12][C:13]([OH:15])=[O:14])#[N:11].[C:16](O)(=O)C.C([O-])(=O)C.[NH4+]>C(O)C>[C:10]([C:12](=[CH:9][C:1]1[CH:6]=[CH:5][C:4]([CH3:16])=[CH:3][CH:2]=1)[C:13]([OH:15])=[O:14])#[N:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9740Cyanoacetic acidHCID 107222-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 31401280540-68-7

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 g of tolualdehyde, 311 g of cyanoacetic acid, 60 ml of acetic acid and 25.6 g of ammonium acetate were refluxed in 1.6 liters of ethyl alcohol for 4 hours with heating. After the reaction, the mixture was concentrated to 600 ml by removing the ethyl alcohol under a reduced pressure, followed by pouring into 1 liter of ice water to separate crystals. The separated crystals were collected by suction filtration and recrystallized from 2 liters of ethyl alcohol to obtain 560 g of 2-cyano-3-(4-methylphenyl)acrylic acid having a melting point of 210 to 215° C. 320 g of the resulting compound and 252 g of thionyl chloride were dissolved in 200 ml of acetonitrile with heating for 1 hour. After the reaction, the acetonitrile and the thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution containing 244.8 g of hydroxyethyl methacrylate, 149 g of pyridine and 2 liters of acetonitrile. The reaction was carried out for 2 hours while maintaining the reaction temperature below 40° C. After the reaction, the reacting solution was poured into ice water to separate crystals, and the resulting crystals were recrystallized from 3 liters of ethyl alcohol to obtain 360 g of the desired compound having a melting point of 74° to 75° C. The identification of the compound was carried out using IR spectrum, NMR spectrum and elemental analysis.

Workup

  1. temperaturewith heating
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated to 600 ml
  4. customby removing the ethyl alcohol under a reduced pressure
  5. additionby pouring into 1 liter of ice water
  6. customto separate crystals
  7. filtrationThe separated crystals were collected by suction filtration
  8. customrecrystallized from 2 liters of ethyl alcohol

Sources & evidence

ORD record
ord-dbc9d5a08b0445399bc86c7296fb513a
Source dataset
uspto-grants-1984_08
Patent number
US04464463

Reaction notes

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