Sulfuric Acid → p-Toluenesulfonic acid

HRID 1279928Notes

Reaction equation

HRID 1279928 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[C:6]1([CH3:16])[C:7](S(O)(=O)=O)=[CH:8][CH:9]=[CH:10][CH:11]=1.C1(C)C=CC=C(S(O)(=O)=O)C=1>C1(C)C=CC=CC=1>[C:6]1([CH3:16])[CH:7]=[CH:8][C:9]([S:1]([OH:3])(=[O:5])=[O:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69252-Methylbenzenesulfonic acidHCID 105362m-Toluenesulfonic acid

Product 1

HCID 6101p-Toluenesulfonic acidYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sulfuric acid (1.0 g, 10.2 mmol) was added to toluene (50.0 g) under the same conditions as Example 1. The analysis by HPLC showed 26% yield p-toluenesulfonic acid, 11% o-toluenesulfonic acid, and 1.3% m-toluenesulfonic acid (ratio p/o=2.4) for a total yield of 38.3%.

Sources & evidence

ORD record
ord-86d6f6b005d94a7b827e0b5c1443f8c9
Source dataset
uspto-grants-2002_09
Patent number
US06448435B1

Reaction notes

Loading…