Synthesis of monoperoxyphthalic acid

Preparation of monoperoxyphthalic acid

Preparation of monoperoxyphthalic acid

Preparation of monoperoxyphthalic acid

A solution of sodium carbonate (62 g, 0.50 mole) in water (250 ml) is placed in a 1-liter flask fitted with a stirrer and thermometer and cooled in ice-salt to 5°C, whereupon 30% hydrogen peroxide (70 g, 0.6 mole) is added in one portion. This mixture is cooled to 0° and treated with finely powdered and sieved phthalic anhydride (75 g, ca. 0.5 mole), then stirred rapidly at —5° to 0° for 30 min or until almost all the anhydride has dissolved. Next the solution is treated in a separatory funnel with ether (350 ml) and shaken with a cold solution of concentrated sulfuric acid (30 ml) in water (150 ml), then extracted three times with ether (150 ml portions). The ether extracts are united, washed with 40 % ammonium sulfate solution (200 ml), and dried overnight in the ice-chest over anhydrous magnesium sulfate (50 g). The content of peroxyphthalic acid is determined by titration. The yield is 78 % (calculated on phthalic anhydride). Crystalline monoperoxyphthalic acid could be prepared according Org. Syn., Coll. Vol. III, 619 (1955).

J. Org. Chem., 24, 1354 (1959)

J Am. Chem. Soc.  77, 3405 (1955)

IUPAC Name

2-carbonoperoxoylbenzoic acid

InChI

InChI=1S/C8H6O5/c9-7(10)5-3-1-2-4-6(5)8(11)13-12/h1-4,12H,(H,9,10)

InChI Key

GLVYLTSKTCWWJR-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C(=C1)C(=O)O)C(=O)OO

MeSH Synonyms

monoperphthalic acid, perphthalate

Depositor-Supplied Synonyms

2-carboperoxybenzoic acid, 2311-91-3, 2-carbonoperoxoylbenzoic acid, Benzenecarboperoxoic acid, 2-carboxy-, Monoperphthalic acid, Perphthalic acid, 2-carboperoxybenzoate, Monoperoxyphtalic acid, AC1L2OJ3, AC1Q68NS, SCHEMBL6935, 2-carbonoperoxoyl-benzoic acid, CHEMBL1162414, DTXSID3075200, EINECS 219-003-5, AR-1D9917, NSC240744, ZINC44361745, AKOS008056464, MCULE-6120306346, NSC 240744, NSC-240744, AK517810, OR045937, SC-69883, FT-0658446, X2080, Benzenecarboperoxoic acid, 2-carboxy- (9CI), S01-0507

Removed Synonyms

MolPort-001-780-251, CID75329, 23656-00-0

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