Ethyl cyanoacetate → HCID 23329210, compound

HRID 225157Notes

Reaction equation

HRID 225157 reaction equation
[Na].[C:2]([CH2:4][C:5]([O:7]CC)=[O:6])#[N:3].Cl[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>C(O)C.C1(C)C=CC=CC=1>[C:2]([CH:4]([CH2:11][C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]([OH:7])=[O:6])#[N:3]

Participants

6

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 107572-ChloroacetophenoneHCID 5360545Sodium

Product 1

HCID 23329210HCID 23329210, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

10 g of sodium was dissolved in 200 ml of ethanol. The solution was cooled to 30° C. and 45.2 g of ethyl cyanoacetate was added rapidly. The resulting mixture was cooled to -15° C. and stirred while a warm solution of 62 g of 2-chloroacetophenone in 100 ml of toluene was added over a 15-minute period, with cooling, allowing the temperature of the mixture to rise to 20° C. over a 1-hour period. The mixture was poured in ice/3 N hydrochloric acid, the organic phase was separated, the solvent was evaporated under reduced pressure and the residue was distilled under reduced pressure to give a liquid, bp: 130°-160° C., at 0.01 Torr., which solidified on standing. Recrystallization from cold ether gave the ethyl ester of 2-cyano-4-oxo-4-phenylbutanoic acid (16A), mp: 53°-54° C.

Workup

  1. temperatureThe resulting mixture was cooled to -15° C.
  2. additionwas added over a 15-minute period
  3. temperaturewith cooling
  4. waitto rise to 20° C. over a 1-hour period
  5. customthe organic phase was separated
  6. customthe solvent was evaporated under reduced pressure
  7. distillationthe residue was distilled under reduced pressure
  8. customto give a liquid, bp: 130°-160° C.
  9. customRecrystallization from cold ether

Sources & evidence

ORD record
ord-0cd76d9b26e44eb28ffb1ed4336157e5
Source dataset
uspto-grants-1980_11
Patent number
US04235923

Reaction notes

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