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

HRID 2351789Notes

Reaction equation

HRID 2351789 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.Br>[Ti]>[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

6

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 7918Acetic Anhydride2×HCID 83063p-Acetylphenyl acetate

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 23963TitaniumCatalyst

Conditions

Temperature
300 fahrenheit

Procedure

One hundred and sixty-six (166) g (0.933 mole) of p-acetoxyacetophenone, 100 g (0.98 mole) of acetic anhydride, 250 g (4.17 moles) of acetic acid, 3.5 g (0.0014 mole) of Co(OAc)2.4H2O, 3.5 g (0.0014 mole) of Mn(OAc)2.4H2O, and 4.7 g (0.0028 mole) of 48% HBr were combined in a two-liter titanium-clad autoclave. The reaction mixture was heated to 300° F. and pressurized to 300 psi. Air was introduced at a rate of 0.75 scf/min. During the run, a solution of 54 g (0.53 mole) of acetic anhydride and 13 g (0.217 mole) of acetic acid was added through a pump. The run time was 25 minutes. Analyses of the total reactor effluent and wash showed: p-acetoxybenzoic acid, 87 mole % yield, p-hydroxybenzoic acid, 1.2 mole % yield, and p-acetoxyacetophenone, 3.5 mole % yield.

Workup

  1. additionAir was introduced at a rate of 0.75 scf/min
  2. washAnalyses of the total reactor effluent and wash

Sources & evidence

ORD record
ord-3cebab42f32543268c82c2933d2a9846
Source dataset
uspto-grants-1989_10
Patent number
US04873361

Reaction notes

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