Benzene → p-Toluenesulfonic acid

HRID 482935Notes

Reaction equation

HRID 482935 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)C1C=CC=CC=1.C1C=CC=CC=1>CCOCC>[CH3:12][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 203.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-isopropyl ethyl glycinate (22.9 g, 0.158 mole) and 33.1 g of p-toluenesulfonic acid monohydrate (0.174 mole) were placed in a reaction vessel filtered with a reflux condenser and a Dean-Stark apparatus. Benzyl alcohol (158 ml, 1.53 mole) and 158 ml of benzene (1.77 mole) were added, and the reaction mixture was refluxed for 24 hours. The reaction mixture was cooled to room temperature, and ~800 ml of ether was added. After stirring at -30° C. overnight, the reaction mixture was filtered and the precipitate collected. The precipitate was washed with cold ether to yield 60.97 g of the impure p-toluenesulfonate salt of the title compound.

Workup

  1. filtrationfiltered with a reflux condenser
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe precipitate collected
  5. washThe precipitate was washed with cold ether

Sources & evidence

ORD record
ord-93c50422e0704ced8bad58c5101cdc37
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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