Water → HCID 13322443, compound

HRID 2308764Notes

Reaction equation

HRID 2308764 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][CH3:24])=[CH:18][C:17]=1[C:26]([O:28][CH3:29])=[O:27].O>CN(C)C=O>[CH2:7]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][CH3:24])=[CH:18][C:17]=1[C:26]([O:28][CH3:29])=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 13329482HCID 13329482, compound

Product 1

HCID 13322443HCID 13322443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

38 g of potassium carbonate and 12.65 ml, (14 g) of benzyl chloride are added to 20.8 g of 4'-hydroxy-3'-methoxycarbonylpropiophenone in 100 ml of dimethylformamide. The mixture is heated at 60° C. for 4 hours, with stirring. It is then poured into iced water, the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried and evaporated to dryness. The residual oil crystallises on trituration with pentane. The crystals are filtered off and recrystallised from ethanol. 18 g of crystals melting at 76°-78° C. are collected.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residual oil crystallises on trituration with pentane
  6. filtrationThe crystals are filtered off
  7. customrecrystallised from ethanol
  8. custom18 g of crystals melting at 76°-78° C. are collected

Sources & evidence

ORD record
ord-2cc60f0df5f14ba48221a543f89097eb
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

Loading…