p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1722306Notes

Reaction equation

HRID 1722306 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)(=O)C>[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

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 143.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

361 mg of the N-protected compound obtained in (a) and 360 mg of anisole were dissolved in 4 ml of acetic acid, and 270 mg of p-toluenesulfonic acid monohydrate was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure. Water and benzene were added to the residue, and the aqueous layer was separated. The aqueous layer was washed with benzene and lyophilized to give 350 mg of the p-toluenesulfonate of the captioned compound as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. additionWater and benzene were added to the residue
  3. customthe aqueous layer was separated
  4. washThe aqueous layer was washed with benzene

Sources & evidence

ORD record
ord-f31153a5512a4c06973add2363d62c13
Source dataset
uspto-grants-1989_08
Patent number
US04855287

Reaction notes

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