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

HRID 2084829Notes

Reaction equation

HRID 2084829 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].S([C:15]1[CH:21]=CC(C)=C[CH:16]=1)(O)(=O)=O.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:10][C:15]([CH3:21])([CH3:16])[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, mixed with dimethoxyacetal (35 ml) and a catalytic amount of tosylic acid, and then, heat-refluxed for 6 hours. The resultant was allowed to stand for cooling, alkalified by adding an aqueous sodium hydroxide solution, and extracted with ether. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over manganese sulfate, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1) to give Compound IIbv-a (19.4 g, 60.5%) as a white solid.

Workup

  1. temperaturefor cooling
  2. extractionextracted with ether
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over manganese sulfate
  5. customevaporated under reduced pressure
  6. customfor removing the solvent
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1)
  8. customto give Compound IIbv-a (19.4 g, 60.5%) as a white solid

Sources & evidence

ORD record
ord-ca25ef203d534ca1b2744b1a8713ff30
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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