Catechol → 2,2-Dimethyl-1,3-benzodioxole

HRID 731976Notes

Reaction equation

HRID 731976 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[C:9]1(C)[CH:14]=CC(S(O)(=O)=O)=C[CH:10]=1>C1(C)C=CC=CC=1.CC(C)=O>[CH3:10][C:9]1([CH3:14])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

5

Reactant 2

HCID 289CatecholHCID 6101p-Toluenesulfonic acid

Product 1

HCID 2858692,2-Dimethyl-1,3-benzodioxoleYield 37,840.301%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 10.0 grams (0.091 mole) of catechol in 100 mL of toluene and 100 mL of acetone was stirred and 0.01 gram (catalyst) of para-toluenesulfonic acid was added in one portion. Upon completion of additon the reaction mixture was warmed to reflux where it was maintained during a 48 hour period. After this time the reaction mixture was cooled to ambient temperature, then it was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using petroleum ether as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 3.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureUpon completion of additon the reaction mixture was warmed
  2. temperatureto reflux where it
  3. temperaturewas maintained during a 48 hour period
  4. concentrationit was concentrated under reduced pressure to a residue
  5. customThe residue was purified with column chromatography on silica gel
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db9989efa97a494ab4df51f6336a34cd
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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