Toluene → p-Toluenesulfonic acid

HRID 1934866Notes

Reaction equation

HRID 1934866 reaction equation
[S:1](=[O:4])(=[O:3])=[O:2].[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[CH3:11][C:5]1[CH:6]=[CH:7][C:8]([S:1]([OH:4])(=[O:3])=[O:2])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 24682Sulfur trioxide2×

Product 1

HCID 6101p-Toluenesulfonic acidYield 28%

Conditions

Temperature
50 °C

Procedure

Sulfur trioxide (0.6 g, 7.5 mmol, stabilized, 99% from Aldrich, Milwaukee, Wis.) was weighed into a 100-ml round-bottom flask in the dry box Toluene (50 g) was added to the sulfur trioxide via syringe under an inert atmosphere. The solution was stirred at 50° C. for 22 hours under a nitrogen atmosphere before it was cooled to room temperature. A dark colored oil formed at the bottom of the solution. The toluene and oil layer was extracted with three 10-cc portions of distilled water. The analysis by HPLC showed 28% yield of p-TSA and 5.5% o-TSA (ratio p/o -5.1) for a total yield of 33.5%.

Workup

  1. temperaturewas cooled to room temperature
  2. customA dark colored oil formed at the bottom of the solution
  3. extractionThe toluene and oil layer was extracted with three 10-cc portions of distilled water

Sources & evidence

ORD record
ord-770d386d42d74d5c946ce9ac28b8ca84
Source dataset
uspto-grants-2002_05
Patent number
US06384271B1

Reaction notes

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