Phthalic Anhydride → 3-Nitrophthalic acid

HRID 2292395Notes

Reaction equation

HRID 2292395 reaction equation
ClC1C=CC=C2C(OC(=O)C=12)=[O:6].[N+:13]([C:16]1[CH:26]=[CH:25][CH:24]=[C:18]2[C:19]([O:21][C:22](=[O:23])[C:17]=12)=[O:20])([O-:15])=[O:14].ClCl.C1(=O)OC(=O)C2=CC=CC=C12>>[N+:13]([C:16]1[CH:26]=[CH:25][CH:24]=[C:18]([C:19]([OH:6])=[O:20])[C:17]=1[C:22]([OH:21])=[O:23])([O-:15])=[O:14]

Participants

5

Reactant 4

HCID 6811Phthalic AnhydrideHCID 216313-Nitrophthalic anhydride2×HCID 24526ChlorineHCID 670143-Chlorophthalic anhydride

Product 1

HCID 690433-Nitrophthalic acid

Procedure

3-Chlorophthalic anhydride can also be prepared from 3-nitrophthalic anhydride by replacement of the nitro group by chlorine. The 3-nitrophthalic anhydride needed for this is prepared in three process steps by nitration of phthalic anhydride in moderate yield, by isomer separation of the nitrophthalic acids formed, by fractional crystallization and by conversion to the anhydride of the 3-nitrophthalic acid obtained (M. S. Newman, P. G. Scheurer, J. Am. Chem. Soc. 78 (1956), 5005; Organic Syntheses, Coil. Vol. 1 (1932), 399-401). This multistage and complicated route, which additionally gives poor yields, is not very suitable for industrial use.

Sources & evidence

ORD record
ord-abb16e57b34d498d8d6e475e7843a17e
Source dataset
uspto-grants-1997_11
Patent number
US05683553

Reaction notes

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