p-Toluenesulfonic acid → 4-Methoxy-2,2-dimethyl-1,3-benzodioxole

HRID 1057941

Reaction equation

HRID 1057941 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:10][C:11]([CH3:16])([CH3:12])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 136223-MethoxycatecholHCID 14798Sodium Hydroxide

Product 1

HCID 150610944-Methoxy-2,2-dimethyl-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Methoxycatechol (25 g) was dissolved in benzene, and dimethoxyacetal (35 ml) and a catalytic amount of p-toluenesulfonic acid were added thereto, followed by heating at reflux for 6 hours. After being allowed to stand for cooling, the mixture was adjusted to alkaline with an aqueous solution of sodium hydroxide, followed by extraction with ether. The organic layer was washed with a saturated saline and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1) to give Compound IIbk-a (19.4 g, 60.5%) as a white solid.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 6 hours
  3. temperaturefor cooling
  4. extractionfollowed by extraction with ether
  5. washThe organic layer was washed with a saturated saline
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1)
  9. customto give Compound IIbk-a (19.4 g, 60.5%) as a white solid

Sources & evidence

ORD record
ord-b56b9681518f4d3ebb66dfcc047e363d
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Linked notes

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