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

HRID 1155598Notes

Reaction equation

HRID 1155598 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[C:9]1(C)[CH:14]=CC(S(O)(=O)=O)=C[CH:10]=1.COC(OC)(C)C>>[CH3:10][C:9]1([CH3:14])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

4

Reactant 3

HCID 289CatecholHCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane

Product 1

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

Procedure

The preparation of the 2-substituted-1,3-benzodioxole starting compounds is known to the art. For example, catechol is subjected to dehydration and the resulting mixture is treated with para-toluenesulfonic acid. Thereafter, dimethoxypropane or another dialkoxyalkane within the ambit of this invention is added to this mixture and the final reaction mix is heated to distill off methanol and drive to reaction to completion. The resulting product is isolated as 2,2-dimethyl-1,3-benzodioxole. It is also possible to condense catechol with a ketone, using P2O5, directly, employing a dehydrating agent to drive off water and to thereby form the desired dioxole starting product.

Workup

  1. customthe final reaction
  2. additionmix
  3. temperatureis heated
  4. distillationto distill off methanol and drive
  5. customto reaction to completion

Sources & evidence

ORD record
ord-d9ad957394684f7582dd0473afd5bc1e
Source dataset
uspto-grants-1981_11
Patent number
US04302615

Reaction notes

Loading…