Acetyl chloride → 4-(3,4-Dichlorophenyl)oxane-2,6-dione

HRID 2294991Notes

Reaction equation

HRID 2294991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][C:11](=[O:13])[O:17][C:15](=[O:16])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 18475290HCID 18475290, compound

Product 1

HCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a combination of the product of Step 2 (100 g) and acetyl chloride (300 mL) at reflux for 5 hours. Cool the reaction mixture, azeotrope with toluene, and concentrate under reduced pressure. Slurry he residue with Et2O (250 mL) and filter to afford 3-(3,4-dichlorophenyl)-glutaric anhydride (86 g).

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationconcentrate under reduced pressure
  3. filtrationfilter

Sources & evidence

ORD record
ord-e49e04efd7574a81aa17a46b338ffe89
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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