Furfural → HCID 21445620, compound

HRID 258943Notes

Reaction equation

HRID 258943 reaction equation
N(CCO)(CCO)CCO.[CH:11](=[O:17])[C:12]1[O:16][CH:15]=[CH:14][CH:13]=1.[C:18](#[N:21])[CH:19]=[CH2:20]>CN(C)C=O.C(O)C>[O:16]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:11]([CH:19]([CH3:20])[C:18]#[N:21])=[O:17]

Participants

6

Reactant 3

HCID 7362FurfuralHCID 7618TriethanolamineHCID 7855Acrylonitrile

Product 1

HCID 21445620HCID 21445620, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Following the procedure in Example 1, 29.8 g. (0.2 mol) of triethanolamine are added to 48 g (0.5 mol) of furfuraldehyde and 13.5 g of Catalyst 1 (0.05 mol) in a mixture of 300 ml of dimethylformamide and 300 ml of ethanol and the whole is then brought to the reflux temperature while stirring under a stream of nitrogen. After 30 minutes, the dropwise addition of a solution of 26.5 (0.05 mol) of distilled acrylonitrile in a mixture of 50 ml of dimethylformamide and 50 ml of ethanol, over the course of 41/2 hours, is started. The mixture is then kept at the same temperature for 20 hours. The solvent mixture is distilled off and the residue is taken up in 300 ml of chloroform. The chloroform solution is then washed with water, dilute sodium bicarbonate solution and twice more with water. It is then dried with magnesium sulphate and after filtering the solution the solvent is distilled off. The residue which remains is distilled in an oil pump vacuum. The α-furoylpropionitrile thus obtained is recrystallized from isopropanol.

Workup

  1. waitThe mixture is then kept at the same temperature for 20 hours
  2. distillationThe solvent mixture is distilled off
  3. washThe chloroform solution is then washed with water, dilute sodium bicarbonate solution and twice more with water
  4. dry with materialIt is then dried with magnesium sulphate
  5. filtrationafter filtering the solution the solvent
  6. distillationis distilled off
  7. distillationThe residue which remains is distilled in an oil pump vacuum

Sources & evidence

ORD record
ord-d2ff464d94624d2da219c16eb2d576ac
Source dataset
uspto-grants-1977_07
Patent number
US04035395

Reaction notes

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