Toluene → 2-Methylbenzoic acid

HRID 1266635Notes

Reaction equation

HRID 1266635 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[C:8]1(C)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClC1C=CC=CC=1>[CH3:11][C:10]1[CH:9]=[CH:8][CH:13]=[CH:12][C:2]=1[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 1140TolueneHCID 6422Trifluoroacetic acid

Product 1

HCID 83732-Methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to RhCl3.nH2O (10 mg). To this suspension (the Rh complex was insoluble), K2S2O8 (1.40 g) was added, and the mixture was stirred in air for 15 minutes. After toluene (5 mL) was added, the mixture was stirred under CO for 24 hours, and then analyzed by GC-MS, in a usual manner (see above), with chlorobenzene as an internal standard. No toluic acid formed. When the rhodium chloride-catalyzed reaction was run for 61 hours under similar conditions, about 185 mg of p-toluic acid formed (TON=38).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred under CO for 24 hours

Sources & evidence

ORD record
ord-4111815bb3d04be7801d0da6c448333c
Source dataset
uspto-grants-2003_04
Patent number
US06548698B1

Reaction notes

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