3-(4-Chlorophenyl) glutarate → 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

HRID 1402772Notes

Reaction equation

HRID 1402772 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1>C(Cl)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10](=[O:12])[O:16][C:14](=[O:15])[CH2:13]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 6072763-(4-Chlorophenyl) glutarate

Product 1

HCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dioneYield 95.8%

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

The suspension of commercial 3-(4-chlorophenyl)glutaric acid (15 g) in acetyl chloride (20 ml) was heated to reflux for 2 h. Then precipitation of the product is completed by addition of petrol ether (50 ml) and cooling to rt. The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give 3-(4-chlorophenyl)glutaric anhydride (13.3 g) as colourless crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customThen precipitation of the product
  4. additionis completed by addition of petrol ether (50 ml)
  5. customThe precipitate is isolated by suction filtration
  6. washwashed with petrol ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-88e4c6848f3d4957bb1ead29edf8e365
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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