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

HRID 1200215Notes

Reaction equation

HRID 1200215 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10]([CH3:12])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:9][C:10]1([CH3:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 289CatecholHCID 6101p-Toluenesulfonic acid

Product 1

HCID 2858692,2-Dimethyl-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of catechol (55 g, 0.5 moles), acetone (150 ml), benzene (150 ml) and p-toluenesulfonic acid (15 mg) was refluxed in a Soxlet extractor containing 140 g of baked 4Å molecular sieves for 24 hours, as described in E. R. Cole, et al., Aust. J. Chem. 33, 675 (1980). The sieves were replaced with fresh sieves and refluxing continued for another 24 hours. The solvents were removed in vacuo and the residue was triturated with 1 liter of hexane. The light yellow solution was decanted and washed with 10% NaOH until the washes were colorless. The organic layer was dried (Na2SO4) and evaporated to 32.4 g (43%) of title compound as an oil which was used without further purification.

Workup

  1. temperaturewas refluxed in a Soxlet extractor
  2. additioncontaining 140 g of baked 4Å molecular sieves for 24 hours
  3. temperaturerefluxing
  4. customThe solvents were removed in vacuo
  5. customthe residue was triturated with 1 liter of hexane
  6. customThe light yellow solution was decanted
  7. washwashed with 10% NaOH until the washes
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. customevaporated to 32.4 g (43%) of title compound as an oil which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-fa44636bc5c34bd3877bbfe92658731b
Source dataset
uspto-grants-1990_02
Patent number
US04904775

Reaction notes

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