Benzoic Acid → 3-Hydroxyphthalic anhydride

HRID 465740Notes

Reaction equation

HRID 465740 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[F-].[K+].[C:15]([OH:23])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[C:15]([O:23][C:11]1[CH:12]=[CH:2][CH:3]=[C:4]2[C:9]([O:8][C:6](=[O:7])[C:5]=12)=[O:10])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH:22][C:11]1[CH:12]=[CH:2][CH:3]=[C:4]2[C:9]([O:8][C:6](=[O:7])[C:5]=12)=[O:10]

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 522689Potassium Fluoride

Product 2

HCID 965803-Hydroxyphthalic anhydrideHCID 570478001,3-Dioxo-1,3-dihydro-2-benzofuran-4-yl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluorophthalic anhydride (0.44 g, 2.6 mmol shown as FPAN in table below), potassium fluoride (Aldrich, 0.18 g, 3.1 mmol), benzoic acid (Aldrich, 0.28 g, 2.3 mmol shown as BzOH in table below) and dimethyl formamide (Aldrich, 3 ml) were heated in a 160° C. oil bath. The reaction was monitored by GC and showed the following results (BOPAN=benzoyloxyphthalic anhydride; ODPAN=oxydiphthalic anhydride; and HOPAN=hydroxyphthalic anhydride):

Sources & evidence

ORD record
ord-b2d3f50670884df88f1d4b0277c68bd5
Source dataset
uspto-grants-1992_10
Patent number
US05153335

Reaction notes

Loading…