2,3,4,5,6-Pentafluorobenzyl Alcohol → 4-Methoxy-2,3,5,6-tetrafluorobenzyl alcohol

HRID 1583460Notes

Reaction equation

HRID 1583460 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:10])[C:5]([F:11])=[C:4](F)[C:3]=1[F:13].[CH3:14][O-:15].[Na+].[Na]>CO>[CH3:14][O:15][C:4]1[C:3]([F:13])=[C:2]([F:1])[C:7]([CH2:8][OH:9])=[C:6]([F:10])[C:5]=1[F:11]

Participants

5

Reactant 3

HCID 99232,3,4,5,6-Pentafluorobenzyl AlcoholHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 119618954-Methoxy-2,3,5,6-tetrafluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pentafluorobenzyl alcohol (1.98 g) was added to a stirred solution of sodium methoxide (obtained by dissolving sodium (0.4 g) in methyl alcohol (10 ml) at the ambient temperature, and the mixture heated at the reflux temperature for 3.5 hours. After cooling the mixture, the solvent was removed by evaporation under reduced pressure and the residue partitioned between water and diethyl ether. After separating the ethereal layer and washing with water, it was dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure to yield 4-methoxy-2,3,5,6-tetrafluorobenzyl alcohol (1.8 g), identical with the product of Example 5.

Workup

  1. customobtained
  2. temperaturethe mixture heated at the reflux temperature for 3.5 hours
  3. temperatureAfter cooling the mixture
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customthe residue partitioned between water and diethyl ether
  6. customAfter separating the ethereal layer
  7. washwashing with water, it
  8. dry with materialwas dried over anhydrous magnesium sulphate
  9. concentrationconcentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c2cc50b9b2214ca29e5053cab732dddc
Source dataset
uspto-grants-1985_11
Patent number
US04551546

Reaction notes

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