Sodium Bicarbonate → 2,3,5,6-Tetrafluorobenzenedimethanol

HRID 1072271Notes

Reaction equation

HRID 1072271 reaction equation
[F:1][C:2]1(CN)[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[CH:3]1[CH2:11]N.N([O-])=[O:16].[Na+].[C:19](=[O:22])([O-])O.[Na+]>C(O)(=O)C.O>[F:1][C:2]1([CH2:19][OH:22])[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[CH:3]1[CH2:11][OH:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 688633712,3,5,6-Tetrafluoroxylylenediamine

Product 1

HCID 667129532,3,5,6-TetrafluorobenzenedimethanolYield 450.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Into a 200 ml-volume flask equipped with a thermometer, a stirring unit, a nitrogen inlet and a reflux condenser, 10.4 g (50.0 mmol) of 2,3,5,6-tetrafluoroxylylenediamine synthesized in Example 1, 50 g of water and 10.35 g (150.0 mmol) of sodium nitrite were charged, and the mixture was stirred at room temperature for 30 minutes. Subsequently, under cooling of the reactor in a water bath, 7.51 g (125.0 mmol) of acetic acid was added dropwise over 60 minutes while keeping the inside of the reaction system at 40° C. or less. After the completion of dropwise addition of acetic acid, 0.8 g of sodium hydrogencarbonate was charged, and the mixture solution was further stirred at 40° C. for 60 minutes. The reaction solution obtained was extracted with 10.0 g of methyl ethyl ketone, the organic phase was washed with 5.0 g of an aqueous 5 mass % sulfuric acid solution, and then the methyl ethyl ketone was removed by distillation, as a result, 9.1 g of 2,3,5,6-tetrafluorobenzenedimethanol was obtained as white crystals. The purity determined from the GC area in percentage was 98.9% and the yield was 85.7%.

Workup

  1. customInto a 200 ml-volume flask equipped with a thermometer
  2. temperatureSubsequently, under cooling of the reactor in a water bath
  3. customat 40° C. or less
  4. additionwas charged
  5. stirringthe mixture solution was further stirred at 40° C. for 60 minutes
  6. customThe reaction solution obtained
  7. extractionwas extracted with 10.0 g of methyl ethyl ketone
  8. washthe organic phase was washed with 5.0 g of an aqueous 5 mass % sulfuric acid solution
  9. customthe methyl ethyl ketone was removed by distillation, as a result

Sources & evidence

ORD record
ord-0b04f98a7676479fb0ee38c08bf2883d
Source dataset
uspto-grants-2005_06
Patent number
US06909023B2

Reaction notes

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