Acetic Acid → Benzoic acid, 4-(acetyloxy)-

HRID 2351787Notes

Reaction equation

HRID 2351787 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])C)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=[O:16])C.C(O)(=O)C>>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:16])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 83063p-Acetylphenyl acetate

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-Yield 73%

Procedure

The oxidation of p-acetoxyacetophenone proceeded as in Example I, except that the reaction was run for 30 minutes and a total of 150 g (1.47 moles) of acetic anhydride and 37 g (0.62 mole) of acetic acid was added through the pump. The reaction mixture was concentrated from 772 g to 413 g by evaporation of acetic acid. The slurry was filtered to remove precipitated p-acetoxybenzoic acid. After drying, 128.2 g of p-acetoxybenzoic acid of 95 mole % purity (73% yield) were obtained. Remaining in the filtrate were: p-acetoxybenzoic acid, 8.5 mole % yield, p-acetoxyacetophenone, 1.8 mole % yield, p-hydroxybenzoic acid, 0.6 mole % yield. Analysis of the reactor wash showed 2.6 mole % p-acetoxybenzoic acid. Total reaction yield of p-acetoxybenzoic acid was 84 mole %.

Workup

  1. concentrationThe reaction mixture was concentrated from 772 g to 413 g by evaporation of acetic acid
  2. filtrationThe slurry was filtered
  3. customto remove
  4. customprecipitated p-acetoxybenzoic acid
  5. customAfter drying

Sources & evidence

ORD record
ord-de40f7f7f1614b808ef8daf65461d46c
Source dataset
uspto-grants-1989_10
Patent number
US04873361

Reaction notes

Loading…