Catechol → HCID 54215771, compound

HRID 1584001Notes

Reaction equation

HRID 1584001 reaction equation
Cl[CH:2]([F:4])[F:3].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].O1CCOC[CH2:24]1>O>[F:3][CH:2]([F:4])[CH2:24][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]

Participants

7

Reactant 5

HCID 289CatecholHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 312751,4-Dioxane

Product 1

HCID 54215771HCID 54215771, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Analogously to L. N. Sedova et al., Zh. Org. Khim. 6, 568 (1970), 275 g of chlorodifluoromethane are passed into a solution of 100 g of o-dihydroxy-benzene, 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. After distillation at 61°-62° C./1.0-1.1 kPa a mixture of 1,2-bis(difluoromethoxy)benzene and 2-difluoroethoxyphenol is obtained, which is separated by chromatography on silica gel with 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-0c758b35c4354ab496499eba21ee949b
Source dataset
uspto-grants-1985_11
Patent number
US04555518

Reaction notes

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