Methanesulfonic Acid → P-Toluic Acid

HRID 436313Notes

Reaction equation

HRID 436313 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]([O:9]C(C2C=CC(C)=CC=2)=O)=[O:8])=[CH:3][CH:2]=1.CS(O)(=O)=O>[N+](C)([O-])=O>[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 1394134-Methylbenzoic acid anhydride

Product 1

HCID 7470P-Toluic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

25.4 g (0.1 mole) of para-toluic anhydride was dissolved in 100 ml of warm nitromethane and then 9.6 g (0.1 mole) of methane sulfonic acid was added. The reaction mixture was stirred for 20 minutes and then filtered, giving 13.72 g (0.1 mole) of para-toluic acid precipitant. The reaction was quantitative, resulting in the para-toluic methane sulfonic anhydride dissolved in nitromethane.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-d8010dacc4c4427e9aee3d8eaf79fcba
Source dataset
uspto-grants-1977_02
Patent number
US04008271

Reaction notes

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