Catechol → 2-(Difluoromethoxy)phenol

HRID 845525Notes

Reaction equation

HRID 845525 reaction equation
Cl[CH:2]([F:4])[F:3].[C:5]1([C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8])[OH:6].[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.O1CCOCC1>[F:3][CH:2]([F:4])[O:6][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[OH:8]

Participants

7

Reactant 4

HCID 289CatecholHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 24489Sodium Dithionite

Product 1

HCID 27741212-(Difluoromethoxy)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

275 g of chlorodifluoromethane are passed into a solution of 100 g of pyrocatechol, 220 g of sodium hydroxide and 60 g of sodium dithionite in 500 ml of water and 400 ml of dioxane at 50°-55° C. analogously to L. N. Sedova et al., Zh. Org. Khim. 6, 568 (1970). After distillation at 61°-62° C./1.0-1.1 kPa, a mixture of 1,2-bis(difluoromethoxy)benzene and 2-difluoromethoxyphenol is obtained, the products being separated by chromatography on silica gel by means of cyclohexane/ethyl acetate (4:1).

Workup

  1. distillationAfter distillation at 61°-62° C./1.0-1.1 kPa
  2. additiona mixture of 1,2-bis(difluoromethoxy)benzene

Sources & evidence

ORD record
ord-11043cf788bb4a68a38d8a22af02a423
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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