p-Toluenesulfonic acid → HCID 19081167, compound

HRID 963504Notes

Reaction equation

HRID 963504 reaction equation
[CH:1]([C:3]1[S:4][C:5]([CH3:8])=[CH:6][CH:7]=1)=[O:2].[CH:9]([O-])([O-])[O:10]C.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:14][O:2][CH:1]([O:10][CH3:9])[C:3]1[S:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 53629101Methylorthoformate

Product 1

HCID 19081167HCID 19081167, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-formyl-5-methylthiophene (12.6 g, 0.1 mol), methyl orthoformate (31.8 g) and a catalytic amount of p-toluene-sulfonic acid in toluene (120 ml) was refluxed for 6 hours. To the cooled reaction mixture was added ethyl acetate and washed with water twice. The organic layer was dried over magnesium sulfate. Removal of the solvent gave a brownish oil, which was purified by distillation under reduced pressure to afford 2-dimethoxymethyl-5-methylthiophene (13.54 g, 78.5% yield) as a yellow oil.

Workup

  1. customTo the cooled reaction mixture
  2. washwashed with water twice
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customRemoval of the solvent
  5. customgave a brownish oil, which
  6. distillationwas purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-222a53e0fd964792a3b3be06146c9e16
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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