Acetyl chloride → Phenylsuccinic Anhydride

HRID 274324Notes

Reaction equation

HRID 274324 reaction equation
[C:1]1([CH:7]([CH2:11][C:12]([OH:14])=[O:13])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C>C1(C)C=CC=CC=1>[C:1]1([CH:7]2[CH2:11][C:12](=[O:13])[O:14][C:8]2=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 95459Phenylsuccinic acid

Product 1

HCID 136911Phenylsuccinic AnhydrideYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of phenylsuccinic acid (20.0 g, 0.10 mol), acetyl chloride, and 200 mL of toluene was stirred at reflux for 5.5 hours, removing H2O azeotropically during the reaction. After cooling to room temperature, toluene was evaporated in vacuo, and the residue was crystallized from ether to obtain 12.2 g of phenyl succinic anhydride as a white solid.

Workup

  1. temperatureat reflux for 5.5 hours
  2. customremoving H2O
  3. customazeotropically during the reaction
  4. customtoluene was evaporated in vacuo
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-e75f300991c6444c9374936561666c4b
Source dataset
uspto-grants-1995_02
Patent number
US05389638

Reaction notes

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