Pyrogallol → 2-Methoxy-2H-1,3-benzodioxol-4-ol

HRID 461796Notes

Reaction equation

HRID 461796 reaction equation
[C:1]1([CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:3]=1[OH:4])[OH:2].[CH:10](OC)(OC)[O:11][CH3:12].ClC(Cl)C>ClCCCl>[OH:2][C:1]1[C:3]2[O:4][CH:10]([O:11][CH3:12])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1057PyrogallolHCID 63651,1-DichloroethaneHCID 9005Trimethyl orthoformate

Product 1

HCID 166648262-Methoxy-2H-1,3-benzodioxol-4-ol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of pyrogallol (25 parts), trimethyl orthoformate (32 parts) and 1,2-dichloroethane (250 parts) was heated with continuous distillation of the solvent for 4 hours. The volume of solvent was kept constant by simultaneous addition of dichloroethane. The mixture was then washed three times with water and dried over sodium sulphate. Removal of the solvent under reduced pressure and distillation of the residue gave 4-hydroxy-2-methoxy-1,3-benzodioxole, boiling point 104°-105° C/1 mmHg.

Workup

  1. temperaturewas heated with continuous distillation of the solvent for 4 hours
  2. washThe mixture was then washed three times with water
  3. dry with materialdried over sodium sulphate
  4. customRemoval of the solvent
  5. distillationunder reduced pressure and distillation of the residue

Sources & evidence

ORD record
ord-ed449280970d4f9d83e52779e91df688
Source dataset
uspto-grants-1977_12
Patent number
US04064250

Reaction notes

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