Hydroquinone → HCID 14618049, compound

HRID 981369Notes

Reaction equation

HRID 981369 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Na].[CH3:10][O-:11].[Na+].F[C:14]1[C:18]([F:20])([F:19])[C:17]([F:22])([F:21])[C:16]([F:24])([F:23])[C:15]=1F>CO.O.CN(C)C=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:14]2[C:18]([F:20])([F:19])[C:17]([F:22])([F:21])[C:16]([F:24])([F:23])[C:15]=2[O:11][C:10]2[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 785HydroquinoneHCID 11212PerfluorocyclopenteneHCID 5360545Sodium2×HCID 10942334Sodium Methoxide

Product 1

HCID 14618049HCID 14618049, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

100 g (1.0 mol) of hydroquinone were dissolved in 200 ml of methanol with heating and converted into the monosodium salt using 180 g of 30% strength by weight sodium methoxide solution. 132 g (1.0 mol) of the sodium salt were then added in portions at 5° C. to a mixture of 250 ml of dimethylformamide and 106 g (0.5 mol) of perfluorocyclopentene. After stirring at room temperature for 19 hours, the mixture was added to 500 ml of water, and the organic phase was separated off after addition of 1000 ml of methylene chloride and subsequently washed with 500 ml of water. After drying, the solvent was stripped off on a rotary evaporator. 177 g of a partly crystalline, oily material remained. For further purification, this was dissolved in 200 ml of ethanol and reprecipitated by addition of 100 ml of water. 143 g of a slightly oily product was obtained, which corresponds to 73% of theory. The spectroscopic data (mass spectrum and 19F nuclear magnetic resonance spectrum) corresponded to the product from Example 44a).

Workup

  1. temperaturewith heating
  2. customthe organic phase was separated off
  3. additionafter addition of 1000 ml of methylene chloride
  4. washsubsequently washed with 500 ml of water
  5. customAfter drying
  6. customthe solvent was stripped off on a rotary evaporator
  7. customFor further purification
  8. dissolutionthis was dissolved in 200 ml of ethanol
  9. customreprecipitated by addition of 100 ml of water
  10. custom143 g of a slightly oily product was obtained

Sources & evidence

ORD record
ord-a11601314b9148a3bfe63dcd5b25a375
Source dataset
uspto-grants-1991_02
Patent number
US04990633

Reaction notes

Loading…