Benzoic Acid → 4-Hydroxybenzoic Acid

HRID 1287683Notes

Reaction equation

[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:10].[OH-].[Na+].OO>C(#N)C>[OH:10][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([OH:9])=[O:8].[OH:10][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([OH:9])=[O:8].[OH:10][C:5]1[CH:6]=[CH:7][C:2]([C:1]([OH:9])=[O:8])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stainless steel autoclave containing 20.0 grams of acetonitrile is charged 122.0 grams (1.0 mole) of benzoic acid and 500 grams of water containing 200 grams (5.0 mole) of sodium hydroxide. Following this, 12.0 grams of a 30% aqueous hydrogen peroxide solution is added to the autoclave during a period of 20 minutes. During the addition of the aqueous hydrogen peroxide solution, the autoclave is maintained at a temperature of 50° C. and atmospheric pressure. At the end of the addition time, heating is discontinued, the autoclave is allowed to return to room temperature and the reaction product is transferred to a clean dry beaker. The product is acidified, extracted with ether and the ether layer is evaporated to produce a crude product. Fractional crystallization of the crude product in water and alcohol will yield essentially pure 2-hydroxybenzoic acid, 3-hydroxybenzoic acid and 4-hydroxybenzoic acid.

Workup

additionis added to the autoclave during a period of 20 minutes
temperatureAt the end of the addition time, heating
customto return to room temperature
extractionextracted with ether
customthe ether layer is evaporated
customto produce a crude product
customFractional crystallization of the crude product in water and alcohol

Sources & evidence

ORD record: ord-b996117cd81c4f0ba148f008b324385b
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985796

Reaction notes

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