p-Toluenesulfonic acid monohydrate → HCID 67868427, compound

HRID 467289Notes

Reaction equation

HRID 467289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[CH2:17][C:18]([OH:20])=[O:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:18]([OH:20])(=[O:19])[CH3:17].[CH3:17][C:11]1[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=1[NH:9][C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 30525665-Hydroxydiclofenac

Product 1

HCID 67868427HCID 67868427, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the acid of Step E, above (2.0 g, 6.4 mmol) in 20 mL of methanol containing a few mg of p-toluene sulfonic acid monohydrate is heated at reflux for 3 hours. The solvent is evaporated in vacuo and the residue dissolved in ethyl acetate. The organic phase is washed with saturated NaHCO3, brine and dried (MgSO4). Removal of solvent affords the product (1.9 g, 90%) as a brown foam. It is used as such in the next step.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent is evaporated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe organic phase is washed with saturated NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-320cad30f9e642d0981bd5322cbbd22a
Source dataset
uspto-grants-1992_10
Patent number
US05159085

Reaction notes

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