4-Hydroxybenzoic Acid → Benzophenone, 4,4'-bisacetyloxy-

HRID 224473Notes

Reaction equation

HRID 224473 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1.F>O>[C:9]([O:7][C:1]1[CH:6]=[CH:5][C:4]([C:13]([C:12]2[CH:11]=[CH:10][C:9]([O:8][C:13](=[O:15])[CH3:12])=[CH:17][CH:16]=2)=[O:15])=[CH:3][CH:2]=1)(=[O:8])[CH3:10]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 996PhenolHCID 14917Hydrofluoric Acid

Product 1

HCID 220136Benzophenone, 4,4'-bisacetyloxy-Yield 151.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45.5 g (0.52 mole) of phenol, 69.0 g (0.50 mole) of 4-hydroxybenzoic acid, and 500 mL of hydrogen fluoride were heated together for 6 hr under autogenous pressure in an autoclave. Then the contents were mixed in excess water to precipitate a pink solid. Yield was 99 g (92.5%). The crude product was acetylated directly, without purification, by refluxing 2 hr in 3 times its volume of acetic anhydride and about 8 drops of sulfuric acid. Precipitation in excess water yielded 113 g of 4,4'-diacetoxybenzophenone of such high purity that no recrystallization was required (melting point 150-152° C. ).

Workup

  1. customto precipitate a pink solid
  2. customThe crude product was acetylated directly, without purification
  3. temperatureby refluxing 2 hr in 3 times its volume of acetic anhydride and about 8 drops of sulfuric acid
  4. customPrecipitation in excess water

Sources & evidence

ORD record
ord-2512b643f30a4e2c8e36314e3fa47e6c
Source dataset
uspto-grants-1980_11
Patent number
US04232143

Reaction notes

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