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

HRID 745580Notes

Reaction equation

HRID 745580 reaction equation
Cl.[C:2]1([C:4](=[CH:6][CH:7]=[CH:8][CH:9]=1)[OH:5])[OH:3].[CH3:10][C:11]([CH3:13])=O>>[CH3:10][C:11]1([CH3:13])[O:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[O:3]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 289CatecholHCID 313Hydrochloric Acid

Product 1

HCID 2858692,2-Dimethyl-1,3-benzodioxoleYield 26%

Procedure

Hydrogen chloride gas was introduced into a solution of 110.1 g of pyrocatechol in 370 ml of acetone for 2 hours while stirring and cooling with ice 10°-15° C. internal temperature, and then for an additional 30 minutes at 0° C. The mixture was poured into ice/water, made alkaline and extracted three times with 1 l of ether. The organic phase was washed neutral three times with 500 ml of water, dried over sodium sulfate and evaporated in vacuo. The residue was distilled in vacuo (b.p. 11 mm/59°-60° C.). There were obtained 39.0 g (26.0% of theory) of 2,2-dimethyl-1,3-benzodioxole.

Workup

  1. temperaturecooling with ice 10°-15° C. internal temperature
  2. extractionextracted three times with 1 l of ether
  3. washThe organic phase was washed neutral three times with 500 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. distillationThe residue was distilled in vacuo (b.p. 11 mm/59°-60° C.)

Sources & evidence

ORD record
ord-e4b660aebdb64138a716a40c69b43683
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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