Acetic Anhydride → 81384-43-2

HRID 463445Notes

Reaction equation

HRID 463445 reaction equation
[CH2:1]([NH:8][C:9](=[O:18])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[CH2:1]([NH:8][C:9](=[O:18])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:11][C:19](=[O:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic Anhydride2×HCID 222718N-Benzyl-2-hydroxy-2-phenylacetamide

Product 1

HCID 515802381384-43-2

Conditions

Temperature
60 °C

Procedure

N-benzyl mandelic amide 100 g is suspended in 250 ml of acetic anhydride and the mixture is heated to 60 degrees C. After all the solid materials have been dissolved in acetic anhydride concentrated sulfuric acid 0.5 ml is added to the solution. Acetylation takes place instantly with exothermic reaction and the reaction mixture turns reddish in color. After the initial exothermic reaction has subsided the mixture is heated to 90-100 degrees C. for 5 hours to complete the acetylation. The reaction mixture is then evaporated at 70-80 degrees C. in vacuum to remove acetic acid, water and the like. The residue is mixed with 300 ml of chloroform. The chloroform layer is washed with 300 ml of 5% aqueous sodium bicarbonate solution, water and dried over anhydrous sodium sulfate. On evaporation of chloroform solution crystalline product 113 g is obtained.

Workup

  1. additionis added to the solution
  2. custominstantly with exothermic reaction
  3. customAfter the initial exothermic reaction
  4. temperatureis heated to 90-100 degrees C
  5. customThe reaction mixture is then evaporated at 70-80 degrees C
  6. customin vacuum to remove acetic acid, water
  7. additionThe residue is mixed with 300 ml of chloroform
  8. washThe chloroform layer is washed with 300 ml of 5% aqueous sodium bicarbonate solution, water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customOn evaporation of chloroform solution crystalline product 113 g
  11. customis obtained

Sources & evidence

ORD record
ord-772fb9e721854b678d1e4d913458ea06
Source dataset
uspto-grants-1985_05
Patent number
US04518789

Reaction notes

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