Acetic Acid → Benzaldehyde

HRID 2259466Notes

Reaction equation

HRID 2259466 reaction equation
BrBr.[C:3]([OH:6])(=[O:5])[CH3:4].OO.[C:9]1([CH3:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH2:3]([OH:6])[C:4]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1.[CH:15](=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:3]([OH:6])(=[O:5])[C:4]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 1140Toluene2×HCID 24408Bromine

Product 3

HCID 240BenzaldehydeYield 31.54%HCID 243Benzoic AcidYield 25.18%HCID 244Benzyl AlcoholYield 6.6%

Reagents, catalysts & solvents 1

HCID 61372Cobalt(II) acetate tetrahydrateCatalyst

Procedure

The procedure of Example I was repeated, but this time Cobalt (II) acetate tetrahydrate (0.5 g, 0,002 moles), bromine (0.5 g, 0,003 moles), toluene (2.58 g, 0.028 moles), acetic acid (25 g) and hydrogen peroxide (35%, 0.22 moles) were used. The total reaction time was 3 hours. The analysis of the reaction mixture revealed that 79.2% of the toluene had been consumed, yielding products including benzylalcohol (6.6% yield), benzaldehyde (31.54% yield) and benzoic acid (25.18% yield).

Workup

  1. customhad been consumed
  2. customyielding products

Sources & evidence

ORD record
ord-13ea0da26cf546538b4213b520b61602
Source dataset
uspto-grants-1995_12
Patent number
US05473101

Reaction notes

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