Toluene → p-Toluenesulfonic acid

HRID 1743365Notes

Reaction equation

HRID 1743365 reaction equation
F[C:2](F)(F)[S:3]([O-:6])(=[O:5])=[O:4].C([N+]1C=CN(C)C=1)CC[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:25]1([CH3:31])[CH:30]=[CH:29]C=[CH:27][CH:26]=1.[S:32](=[O:35])(=[O:34])=[O:33]>>[C:25]1([CH3:31])[CH:30]=[CH:29][C:2]([S:3]([OH:6])(=[O:5])=[O:4])=[CH:27][CH:26]=1.[C:13]1([CH3:12])[C:18]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24682Sulfur trioxideHCID 178443379HCID 178443379, compound

Product 2

HCID 6101p-Toluenesulfonic acidYield 77%HCID 69252-Methylbenzenesulfonic acidYield 22%

Procedure

In a round-bottomed flask (25 cm3) equipped with a magnetic stirrer flea and stopper, 1-decyl-3-methylimidazolium trifluoromethanesulfonate (0.97 g, 2.5 mmol) and toluene (0.46g, 5.0 mmol) were added. Sulfur trioxide (0.44g, 5.5 mmol) was cautiously added (carried out in a dry box) and the mixture stirred for 1 hour. A crude sample was taken from the flask and analysed by NMR (CDCl3, 300 MHz). This showed that the reaction was complete and gave 77% of p-toluenesulfonic acid and 22% o-toluenesulfonic acid. The products were isolated from the ionic liquid by Kugelrohr distillation at 1 mmHg. This gave colourless solid (bp=200° C. at 1 mmHg). The structures were confirmed by NMR analysis and were in accordance with authentic material.

Workup

  1. additionwere added
  2. customcarried out in a dry box

Sources & evidence

ORD record
ord-e14775365a1a4ce2af6f895296d7419c
Source dataset
uspto-grants-2006_03
Patent number
US07009077B2

Reaction notes

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