Sodium Chloride → 3'-Chloroacetamidomethyl-4'-hydroxypropiophenone

HRID 247738

Reaction equation

HRID 247738 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.O[CH2:13][NH:14][C:15](=[O:18])[CH2:16][Cl:17].[Cl-].[Na+]>S(=O)(=O)(O)O>[Cl:17][CH2:16][C:15]([NH:14][CH2:13][C:7]1[CH:6]=[C:5]([C:8](=[O:11])[CH2:9][CH3:10])[CH:4]=[CH:3][C:2]=1[OH:1])=[O:18]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 62714'-HydroxypropiophenoneHCID 62466N-Methylol-alpha-chloroacetamide

Product 1

HCID 136317323'-Chloroacetamidomethyl-4'-hydroxypropiophenoneYield 56.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 40 ml of concentrated sulfuric acid with stirring under ice-cooling is added a mixture of 10 g of 4'-hydroxypropiophenone and 10 g of N-hydroxymethylchloroacetic amide in a small portion. After addition, the reaction mixture is further stirred under ice-cooling for 130 minutes. The resulting mixture is poured into ice-cold water containing sodium chloride and the solution is extracted with ethyl acetate. The ethyl acetate layer is washed with water and dried over sodium sulfate and then filtered. The filtrate is concentrated under reduced pressure and obtained white crystals are recrystallized from a mixture of hexane and ethanol to give 9.6 g of 3'-chloroacetamidomethyl-4'-hydroxypropiophenone as white crystals, melting at 143°-145° C.

Workup

  1. temperaturecooling
  2. additionis added
  3. additionAfter addition
  4. temperaturecooling for 130 minutes
  5. additionThe resulting mixture is poured into ice-cold water
  6. extractionthe solution is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated under reduced pressure
  11. customobtained white crystals
  12. customare recrystallized from a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-632dcacfe34a41d6b24d0d2ec8ea2465
Source dataset
uspto-grants-1987_11
Patent number
US04709095

Linked notes

Loading…