Benzoic Acid → 3-Hydroxyphthalic anhydride

HRID 465741Notes

Reaction equation

HRID 465741 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>CN1C(=O)CCC1>[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 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Fluorophthalic anhydride (0.44 g, 2.6 mmol shown as FPAN in table below), potassium fluoride (Aldrich, 0.14 g, 2.4 mmol), benzoic acid (Aldrich, 0.31 g, 2.5 mmol shown as BzOH in table below) and N-methyl pyrrolidinone (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-ea5c9c60f915492bbcb87391e03880bf
Source dataset
uspto-grants-1992_10
Patent number
US05153335

Reaction notes

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