3-Phenylglutaric acid → 4-Phenyloxane-2,6-dione

HRID 1402777Notes

Reaction equation

HRID 1402777 reaction equation
[C:1]1([CH:7]([CH2:12][C:13]([OH:15])=[O:14])[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)(=O)C>[C:1]1([CH:7]2[CH2:8][C:9](=[O:11])[O:15][C:13](=[O:14])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 778233-Phenylglutaric acid

Product 1

HCID 2978824-Phenyloxane-2,6-dioneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

The suspension of 3-phenylglutaric acid (16.39 g) in acetyl chloride (28.6 ml) was heated to reflux with stirring for 2 h. Then precipitation of the product is completed by addition of petrol ether (70 ml) and cooling to rt. The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give 3-phenylglutaric anhydride (13.24 g) as colourless crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThen precipitation of the product
  4. additionis completed by addition of petrol ether (70 ml)
  5. customThe precipitate is isolated by suction filtration
  6. washwashed with petrol ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a8205cfdc8b24760b1e09c9cf45f123b
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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