3-Methylcatechol → 4-Methyl-1,3-benzodioxole

HRID 1376547Notes

Reaction equation

HRID 1376547 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].[OH-].[Na+].Cl[CH2:13]Cl.O>CS(C)=O.C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]2[O:9][CH2:13][O:5][C:4]=2[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 3403-MethylcatecholHCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium Hydroxide

Product 1

HCID 885604-Methyl-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 11.00 g of 3-methylcatechol and 7.09 g of sodium hydroxide in 10 mL of dry dimethylsulfoxide is added 6.34 mL of dichloromethane. A reflux condenser is attached and the mixture heated in an oil bath to 120° C. for 30 minutes. The mixture is allowed to cool to room temperature and then is distributed between 50 mL of water and 200 mL of chloroform. The chloroform layer is dried over magnesium sulfate and concentrated under reduced pressure to yield a red liquid, which is purified by chromatography on silica gel to afford 3.0 g of 4-methyl-1,3-benzodioxole as a light yellow liquid.

Workup

  1. customA reflux condenser is attached
  2. temperatureto cool to room temperature
  3. dry with materialThe chloroform layer is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a red liquid, which
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d5b7d8098d6741c2bde8c533fe9c0bb6
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

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