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

Workup

concentrationAfter concentrating the mixture under reduced pressure (30 mm.Hg)
filtrationAfter filtration
customdrying

Sources & evidence

ORD record: ord-32b5d7c475b04f468a9c379ef539b463
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04131674

Reaction notes

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