Formaldehyde → Ethyl 2-cyanopropionate

HRID 1076277Notes

Reaction equation

HRID 1076277 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]#[N:8])=[O:5].[C:9]1(C=CC(O)=CC=1)O.N1CCCCC1.C=O>[Pd].O.C(O)(=O)C.C1(C)C=CC=CC=1>[C:7]([CH:6]([CH3:9])[C:4]([O:3][CH2:2][CH3:1])=[O:5])#[N:8]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 785HydroquinoneHCID 7764Ethyl cyanoacetateHCID 8082Piperidine2×

Product 1

HCID 98018Ethyl 2-cyanopropionate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

904 Parts of ethyl cyano acetate, 10 parts of hydroquinone, 4.3 parts of piperidine, 45 parts of 3% palladium on charcoal catalyst and 6,500 parts of toluene are mixed at 60°C under an atmosphere of hydrogen maintained at 30 p.s.i.g., 1,000 Parts of a solution made from 1,000 parts of formalin (36%), 75 parts of acetic acid, 86 parts of piperidine and water to give a total of 1,500 parts are added at a uniform rate over 3 hours the temperature being maintained at 60°-65°C. The reaction mixture is cooled, filtered and the toluene layer separated. Distillation under reduced pressure of the toluene layer yields 374.7 parts of ethyl 2-cyanopropionate boiling point 91°-118°C/20 mm. of mercury.

Workup

  1. temperaturemaintained at 30 p.s.i.g
  2. customto give a total of 1,500 parts
  3. additionare added at a uniform rate over 3 hours the temperature
  4. temperaturebeing maintained at 60°-65°C
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. customthe toluene layer separated
  8. distillationDistillation under reduced pressure of the toluene layer

Sources & evidence

ORD record
ord-4437c11b75db4b57901c7a07019b5215
Source dataset
uspto-grants-1976_05
Patent number
US03956357

Reaction notes

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