Glyoxylic Acid → HCID 69861887, compound

HRID 1355335Notes

Reaction equation

HRID 1355335 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+:20].[K+]>CO>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:14]#[N:15])=[CH:2][C:1]([O-:5])=[O:4])=[CH:9][CH:8]=1.[K+:20]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 11430Potassium CarbonateHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 69861887HCID 69861887, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

133 g (0.9 mol) of 50% strength aqueous glyoxylic acid was added dropwise with stirring to 91.2 g (0.6 mol) of (4-chlorophenyl)acetonitrile and 210 g (1.5 mol) of potassium carbonate in 1.2 l of methanol such that the reaction temperature increased to 35° C. The mixture was stirred at room temperature for 6 h and then filtered, and the residue was washed with methylene chloride and dried under reduced pressure. At room temperature, the crude product was stirred with 3 l of water for 1.5 h, and the residue was filtered off, washed with water and dried. Yield: 138 g of a solid of m.p. 241-242° C.

Workup

  1. filtrationfiltered
  2. washthe residue was washed with methylene chloride
  3. customdried under reduced pressure
  4. stirringAt room temperature, the crude product was stirred with 3 l of water for 1.5 h
  5. filtrationthe residue was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-343447a38f3144e391996cad2394e952
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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