Synthesis of peroxybenzoic acid

Preparation of peroxybenzoic acid

Preparation of peroxybenzoic acid

Preparation of peroxybenzoic acid

A solution of 8.0 g. (0.102 mole) of sodium peroxide in 135 ml. of water is prepared with cooling so that the temperature does not exceed 20°. The solution is filtered through a “fine” porosity fritted disk to remove the yellow suspended solids. The filtrate is placed in a 1000-ml. beaker and stirred magnetically while 175 ml. of denatured ethanol and a solution of 0.5 g. of magnesium sulfate heptahydrate in 15 ml. of water are added. Heat liberated during the addition of ethanol raises the temperature of the solution about 8°. When the solution is again at room temperature, 11.6 ml. (0.100 mole) of benzoyl chloride is added dropwise while the solution is stirred magnetically. The addition should take 10 to 12 min. The mixture is filtered to remove any benzoyl peroxide. The filtrate is acidified with 20% sulfuric acid and extracted with carbon tetrachloride, chloroform, or benzene. Six extractions using about 75-ml. portions give 0.075 mole of peroxybenzoic acid.

J. Org. Chem., 1964, 29 (7), pp 2099–2100

Preparation of peroxybenzoic acid

Preparation of peroxybenzoic acid

A solution of dibenzoyl peroxide (10 g) in toluene (20 ml) is cooled, with stirring, to — 5° and then treated during 5 min with a pre-cooled (—2°) solution of sodium (2 g) in 96% ethanol (50 ml). Sodium peroxybenzoate separates at once. To this mixture is added ice water, in which the sodium peroxybenzoate dissolves. The aqueous peroxybenzoate solution is separated from the toluene in a separatory funnel and washed twice with ether which removes residual toluene and ethyl benzoate. This purified aqueous solution is cooled and treated with a mixture of concentrated sulfuric acid (5 g) and ice-water (60 g), and the peroxybenzoic acid liberated is shaken into chloroform (60 ml in two portions). The chloroform extracts are united and the aqueous peroxybenzoate solution is separated from the toluene in a separatory funnel and washed twice with ether which removes residual toluene and ethyl benzoate. This purified aqueous solution is cooled and treated with a mixture of concentrated sulfuric acid (5 g) and ice-water (60 g), and the peroxybenzoic acid liberated is shaken into chloroform (60 ml in two portions). The chloroform extracts are united and the aqueous peroxybenzoate solution is separated from the toluene in a separatory funnel and washed twice with ether which removes residual toluene and ethyl benzoate. This purified aqueous solution is cooled and treated with a mixture of concentrated sulfuric acid (5 g) and ice-water (60 g), and the peroxybenzoic acid liberated is shaken into chloroform (60 ml in two portions). The chloroform extracts are united and dried over sodium sulfate; they may then be used for oxidations. For preparation of crystalline peroxybenzoic acid the chloroform is evaporated in a stream of dry air at ca. 30 mm and 25-30° (heat must never be used when recrystallizing dibenzoyl peroxide!!!). The content of active oxygen is determined by iodometric titration.

Angew. Chem., 65, 57 (1953).

 

IUPAC Name

benzenecarboperoxoic acid

InChI

InChI=1S/C7H6O3/c8-7(10-9)6-4-2-1-3-5-6/h1-5,9H

InChI Key

XCRBXWCUXJNEFX-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

Dentavon, perbenzoic acid, peroxybenzoic acid

Depositor-Supplied Synonyms

Perbenzoic acid, Peroxybenzoic acid, Benzenecarboperoxoic acid, 93-59-4, UNII-C0EZ97V99I, hydroxy-benzoate, benzoperoxoic acid, Kyselina perbenzoova, Kyselina peroxybenzoova, AC1LAXRN, Benzenecarboperoxoic-acid-, SCHEMBL1816, C0EZ97V99I, SCHEMBL8670852, Benzenecarboperoxoic acid (9CI), DTXSID10239223, XCRBXWCUXJNEFX-UHFFFAOYSA-N, ZINC8251250, AKOS006275773, OR038499, 29460-EP2277878A1, 29460-EP2287160A1, 29460-EP2311842A2, 81224-EP2298761A1, 81224-EP2305687A1

Removed Synonyms

hydroxybenzoate, Benzoyl hydroperoxide, Benzoylhydrogen peroxide, Kyselina perbenzoova [Czech], CCRIS 687, Kyselina peroxybenzoova [Czech], EINECS 202-260-2, CID523077, BRN 1210120, 4-09-00-00715 (Beilstein Handbook Reference), PEROXYBENZOIC ACID 4 4′-OXYDI- DI-TERT-BUTYL ESTER

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