Benzoic Acid → 4-Hydroxybenzoic Acid

HRID 1579718Notes

Reaction equation

HRID 1579718 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)C1C=CC=CC=1>[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

8

Reactant 4

HCID 243Benzoic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium Hydroxide

Product 3

HCID 1354-Hydroxybenzoic AcidHCID 338Salicylic AcidHCID 74203-Hydroxybenzoic Acid

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Conditions

Temperature
50 °C

Procedure

In this example 122.0 grams (1.0 moles) of benzoic acid are placed in a stainless steel autoclave containing 15.0 grams of benzonitrile and 500 grams of water containing 200.0 grams (5.0 moles) of sodium hydroxide. Thereafter, 12.0 grams of a 30 percent aqueous hydrogen peroxide solution is added to the autoclave during a period of time comprising 22 minutes. The autoclave is maintained at a temperature of 50°C and a pressure of one atmosphere during the entire 22 minutes of treatment time. At the end of the 22 minutes, the autoclave is allowed to return to room temperature and the treatment product transferred to a clean dry beaker. The treatment product is acidified, extracted with ether and the ether layer evaporated to produce a crude product. Fractional crystallization of the crude product in water and alcohol yields essentially pure 2-hydroxybenzoic acid, 3-hydroxybenzoic acid and 4-hydroxybenzoic acid.

Workup

  1. customduring the entire 22 minutes of treatment time
  2. customAt the end of the 22 minutes
  3. customto return to room temperature
  4. extractionextracted with ether
  5. customthe ether layer evaporated
  6. customto produce a crude product
  7. customFractional crystallization of the crude product in water and alcohol

Sources & evidence

ORD record
ord-e8d6c172ec1a49bc8263729622e7a331
Source dataset
uspto-grants-1976_01
Patent number
US03931295

Reaction notes

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