Acetyl chloride → 4-(1,3-Dioxaindan-5-yl)oxane-2,6-dione

HRID 2256279Notes

Reaction equation

HRID 2256279 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)(=O)C>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH2:11][C:12](=[O:14])[O:18][C:16](=[O:17])[CH2:15]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 332828HCID 332828, compound

Product 1

HCID 219278554-(1,3-Dioxaindan-5-yl)oxane-2,6-dioneYield 97.9%

Procedure

3-(1,3-benzodioxol-5-yl)glutaric acid (3.2 g) was treated with acetyl chloride (15 mL) and the resulting mixture heated at reflux for 5 hours. The cooled reaction mixture was then azeotroped with toluene (2×100 mL) and concentrated under reduced pressure. The residue was slurried with diethyl ether and filtered to afford the title compound (2.91 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 5 hours
  3. customThe cooled reaction mixture
  4. customwas then azeotroped with toluene (2×100 mL)
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8e4d43cfa15241d7b249ba2e450e223c
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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