Catechol → 1,3-Benzodioxole

HRID 2082766Notes

Reaction equation

HRID 2082766 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[OH-].[Na+].[CH2:11](Cl)Cl>CS(C)=O>[CH2:11]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

5

Reactant 3

HCID 289CatecholHCID 6344DichloromethaneHCID 14798Sodium Hydroxide

Product 1

HCID 92291,3-BenzodioxoleYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 110 g. of catechol, 160 g. of 50 percent aqueous sodium hydroxide, and 100 ml. of DMSO was stirred and heated to 95°-100° C. for 15 minutes. The temperature of the solution was maintained in the same range while the solution was added over a period of 30 minutes to a refluxing solution of 100 ml. of methylene dichloride in 400 ml. of DMSO. After the addition, the temperature of the refluxing reaction mixture reached 120° C., and was maintained at this level for 2.5 hours. Following the same isolation procedures as indicated in (A) above, 99.7 g. (80 percent) of methylenedioxybenzene was isolated.

Workup

  1. temperatureheated to 95°-100° C. for 15 minutes
  2. temperatureThe temperature of the solution was maintained in the same range while the solution
  3. additionwas added over a period of 30 minutes to a refluxing solution of 100 ml
  4. additionAfter the addition
  5. customthe temperature of the refluxing reaction mixture
  6. customreached 120° C.
  7. temperaturewas maintained at this level for 2.5 hours

Sources & evidence

ORD record
ord-051c08855c0f4285aa66b0c0dfc18802
Source dataset
uspto-grants-1978_04
Patent number
US04082774

Reaction notes

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