Dimethyl Sulfoxide → 1,3-Benzodioxole, 4,6-dimethyl-

HRID 1090630

Reaction equation

HRID 1090630 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:4]([OH:5])[C:3]=1[OH:10].[CH3:11]S(C)=O.ClCCl.[OH-].[Na+]>O>[CH3:1][C:2]1[C:3]2[O:10][CH2:11][O:5][C:4]=2[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 177373,5-Dimethylbenzene-1,2-diol

Product 1

HCID 199138211,3-Benzodioxole, 4,6-dimethyl-Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dimethylcatechol (13.8 g) in a vigorously stirred mixture of dimethylsulphoxide (150 ml), dichloromethane (10 g) and sodium hydroxide (8.3 g) under nitrogen atmosphere was heated over an oil bath (120°-130° C.) for 2 hours. The mixture was poured into water (600 ml) and extracted (×4) with ether. The ethereal solution was dried and evaporated to afford 3,5-dimethyl-l,2-(methylenedioxy)benzene (14.0 g, 93%) as an oil.

Workup

  1. temperaturewas heated over an oil bath (120°-130° C.) for 2 hours
  2. extractionextracted (×4) with ether
  3. customThe ethereal solution was dried
  4. customevaporated

Sources & evidence

ORD record
ord-f27c214ab15a42449914eb6809591599
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Linked notes

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