Toluene → P-Toluic Acid

HRID 1266633Notes

Reaction equation

HRID 1266633 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[C:8]1([CH3:14])[CH:13]=[CH:12]C=[CH:10][CH:9]=1.[OH-].[Na+]>O>[CH3:14][C:8]1[CH:9]=[CH:10][C:2]([C:3]([OH:5])=[O:4])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 14798Sodium Hydroxide

Product 1

HCID 7470P-Toluic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of K2S2O8 (1.35 g), trifluoroacetic acid (4 mL), and the catalyst solution as prepared in Example 4(a) (1 mL) was stirred in air for 10 minutes. After toluene (5 mL) was added, the mixture was stirred under CO (1 atm) at room temperature for 66 hours. The mixture was diluted with water (5 mL), basified with NaOH, washed with ether, acidified with HCl, and thoroughly extracted with ether. The combined etherial extracts were evaporated to dryness. The residue was sublimed under vacuum to give 225 mg (TON=10) of p-toluic acid of >95% purity (1H NMR).

Workup

  1. stirringthe mixture was stirred under CO (1 atm) at room temperature for 66 hours
  2. washwashed with ether
  3. extractionthoroughly extracted with ether
  4. customThe combined etherial extracts were evaporated to dryness

Sources & evidence

ORD record
ord-e26cf5543ebf46ad8824c2907ae2d29b
Source dataset
uspto-grants-2003_04
Patent number
US06548698B1

Reaction notes

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