Acetic Anhydride → 5-(Trifluoromethyl)isobenzofuran-1,3-dione

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6](=[CH:10][CH:11]=1)[C:7](O)=[O:8].C(OC(=O)C)(=O)C>>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]2[C:12](=[O:14])[O:13][C:7](=[O:8])[C:6]2=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 5990394-(Trifluoromethyl)phthalic acid

Product 1

HCID 127177895-(Trifluoromethyl)isobenzofuran-1,3-dioneYield 74.7%

Procedure

4-Trifluoromethyl-phthalic acid (106.6 g.) and acetic anhydride (215 cc.) are heated to the reflux temperature for 30 minutes. After concentration under reduced pressure (30 mm Hg), the residue is stirred with cyclohexane (420 cc.). After filtration and drying, 4-trifluoromethyl-phthalic anhydride (73.5 g.) melting at 54° C is obtained.

Workup

concentrationAfter concentration under reduced pressure (30 mm Hg)
filtrationAfter filtration
customdrying

Sources & evidence

ORD record: ord-6eae555cb5c84c91b3e011b3515d54ee
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04016274

Reaction notes

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