Methanol → p-Toluenesulfonic acid

HRID 1351136Notes

Reaction equation

HRID 1351136 reaction equation
[C:1]1(C)[C:2]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:12]O>>[C:5]1([CH3:12])[CH:6]=[CH:1][C:2]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 69252-Methylbenzenesulfonic acid

Product 1

HCID 6101p-Toluenesulfonic acid

Procedure

Compound C (250 mg, prepared in analogous fashion to the process described in Example 12 above) was dissolved in methanol (10 mL). Toluenesulphonic acid (110 mg) was added to the solution. The methanol was removed under reduced pressure and the remaining gum was re-dissolved in the minimum amount of hot ethyl acetate possible. The solution was seeded with previously prepared salt (prepared by slow evaporation of solvent from a small portion of a solution of title compound, prepared in analogous fashion to this procedure) and left in the fridge for several days to crystallise. The resulting crystals were collected by filtration and washed with a small amount of cold ethyl acetate (recovered 280 mg, 78%).

Workup

  1. customThe methanol was removed under reduced pressure
  2. dissolutionthe remaining gum was re-dissolved in the minimum amount of hot ethyl acetate possible
  3. customprepared by slow evaporation of solvent from a small portion of a solution of title compound
  4. customprepared in analogous fashion to this procedure) and
  5. waitleft in the fridge for several days
  6. customto crystallise
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with a small amount of cold ethyl acetate (recovered 280 mg, 78%)

Sources & evidence

ORD record
ord-9e8eb687b8f74e5bb42031080d08ebad
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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