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

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

Reactant 2

HCID 6367Acetyl chloride

HCID 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

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

Sources & evidence

ORD record: ord-8e4d43cfa15241d7b249ba2e450e223c
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654316

Reaction notes

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