Ethanol → p-Toluenesulfonic acid

HRID 1697448Notes

Reaction equation

HRID 1697448 reaction equation
C(O)C.O.[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.Cl.O1CCOCC1>C(OCC)(=O)C.C(O)C.C(OCC)(=O)C>[CH3:15][C:5]1[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

A rapidly stirring solution of the free base in ethyl acetate-ethanol or ethanol was treated with either p-toluenesulfonic acid monohydrate (1 equivalent; Aldrich; added as a solution in ethyl acetate) or HCl-dioxane (1-2 equivalent; 4 M; Aldrich) at room temperature. After stirring for 2-16 hours, the precipitate was collected by filtration, rinsed with ethyl acetate, and dried to afford the p-toluenesulfonate salt or the hydrochloride salt.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washrinsed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-49d745850b5f40c6acaca3df35804352
Source dataset
uspto-grants-2012_04
Patent number
US08163916B2

Reaction notes

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