4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

HRID 375263Notes

Reaction equation

HRID 375263 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(OCC)(=[O:21])C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([OH:21])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol produced in Example VIII in dry CH2Cl2 at 0 degree C. there were added triethylamine, p-toluenesulfonyl chloride and N,N-dimethyl-4-aminopyridine (catalytic amount). The mixture was stirred overnight at room temperature, and then diluted with ethyl acetate. The reaction mixture was washed with H2O, saturated aqueous NaHCO3 and brine solution, dried over Na2SO4, and concentrated in vacuo to a yellow oil. Purification by SiO2 column chromatography yielded the p-toluenesulfonate.

Workup

  1. customat 0 degree
  2. washThe reaction mixture was washed with H2O, saturated aqueous NaHCO3 and brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo to a yellow oil
  5. customPurification by SiO2 column chromatography

Sources & evidence

ORD record
ord-92b2cca8c45e412b83570ec182720b59
Source dataset
uspto-grants-1996_01
Patent number
US05484925

Reaction notes

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