p-Toluenesulfonic acid monohydrate → HCID 86720817, compound

HRID 877317

Reaction equation

HRID 877317 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 fit 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 fit
  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-b56a5c9f0c3648a4ab4d0770ff57f6d0
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Linked notes

Loading…