Water → 5-(4-Acetylphenyl)furan-2-carbonitrile

HRID 268092Notes

Reaction equation

HRID 268092 reaction equation
C(C1C=CC(C2OC(C=O)=CC=2)=CC=1)(=O)C.[C:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][C:29]([C:31]#[N:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)(=[O:19])[CH3:18].Cl.NO.O>C(O)C.CN(C)C=O>[C:17]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[O:30][C:29]([C:31]#[N:32])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 21553328HCID 21553328, compound

Product 1

HCID 215533215-(4-Acetylphenyl)furan-2-carbonitrileYield 52.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

5-(p-Acetylphenyl)-2-furonitrile 5-(p-Acetylphenyl)-2-furaldehyde (43 g, 0.2 mole) was dissolved in a mixture of 2.8 l of ethanol and 150 ml of dimethylformamide by warming on a steam bath with stirring. The slightly cloudy brown solution was cooled down to 35° and then 13.9 g (0.2 mole) of hydroxylamine hydrochloride in a minimum amount of water (50 ml) was added in about 5 minutes. The cloudy solution was allowed to stir at ambient temperature for 53/4 hours. After overnight standing, the reaction mixture was poured onto crushed ice. Light brown solid separated and was collected, washed with water and air dried. More solid separated from the filtrate and was also collected. The combined yield of the oxime was 43 g (93.5%). The solid was placed in 500 ml of acetic anhydride and heated at reflux for 4 hours. After cooling, the reaction mixture was poured onto crushed ice and allowed to hydrolyze gradually. The brown solid was collected, washed well with water and air dried to give 37.5 g of crude material. Recrystallization from 1.1 l of methylcyclohexane gave 22 g (52.5%) of 5-(p-acetylphenyl)-2-furonitrile.

Workup

  1. temperatureby warming on a steam bath
  2. temperatureThe slightly cloudy brown solution was cooled down to 35°
  3. stirringto stir at ambient temperature for 53/4 hours
  4. additionthe reaction mixture was poured
  5. customonto crushed ice
  6. customLight brown solid separated
  7. customwas collected
  8. washwashed with water and air
  9. customdried
  10. customMore solid separated from the filtrate
  11. customwas also collected
  12. temperatureheated
  13. temperatureat reflux for 4 hours
  14. temperatureAfter cooling
  15. additionthe reaction mixture was poured
  16. customonto crushed ice
  17. customThe brown solid was collected
  18. washwashed well with water and air
  19. customdried
  20. customto give 37.5 g of crude material
  21. customRecrystallization from 1.1 l of methylcyclohexane

Sources & evidence

ORD record
ord-d07c571e830549909d65050ec42f5e3c
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

Loading…