Toluene → 3-Methylbenzoic acid

HRID 1266636Notes

Reaction equation

HRID 1266636 reaction equation
FC(F)(F)[C:3]([O:5][C:6](=[O:11])[C:7](F)(F)F)=[O:4].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([CH3:20])[CH:15]=[CH:16][CH:17]=[C:7]([C:6]([OH:5])=[O:11])[CH:19]=1.[C:14]1([CH3:20])[C:19]([C:3]([OH:5])=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 9845Trifluoroacetic anhydride

Product 2

HCID 74183-Methylbenzoic acidHCID 83732-Methylbenzoic acid

Conditions

Temperature
200 °C

Procedure

A mixture of toluene (5 mL), trifluoroacetic anhydride (1 mL), and the catalyst solution as prepared above (0.3 mL) was pressurized, at room temperature, with air (1000 psig) and CO (120 psig). The resulting mixture was stirred at 200° C. for 2 hours. After the mixture was cooled down to room temperature, the solvents were evaporated. The residue was redissolved in ether and analyzed by GC-MS with chlorobenzene as an internal standard. A mixture of p-toluic acid and m-toluic acid (70:30) was produced with TON=20, along with trace amounts of o-toluic acid.

Workup

  1. customthe catalyst solution as prepared above (0.3 mL)
  2. customwas pressurized, at room temperature, with air (1000 psig) and CO (120 psig)
  3. temperatureAfter the mixture was cooled down to room temperature
  4. customthe solvents were evaporated
  5. dissolutionThe residue was redissolved in ether
  6. additionA mixture of p-toluic acid

Sources & evidence

ORD record
ord-09d555f9c9224a86971996facbb36cd3
Source dataset
uspto-grants-2003_04
Patent number
US06548698B1

Reaction notes

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