p-Toluenesulfonic acid monohydrate → HCID 86720817, compound

HRID 2205695Notes

Reaction equation

HRID 2205695 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[OH2:15].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54136641Methyl 4-(2-methoxyethenyl)benzoate

Product 1

HCID 86720817HCID 86720817, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was evaporated at reduced pressure
  4. customThe residue was partitioned between DCM and 10% aqueous potassium carbonate
  5. additionThe organic phase was poured through a hydrophobic frit
  6. customthe solvent evaporated at reduced pressure
  7. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-3b09d947aa8f40c78ef32dcc3aff60ad
Source dataset
uspto-grants-2016_06
Patent number
US09371318B2

Reaction notes

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