Water → 2,3,5,6-Tetrafluorobenzenedimethanol
Reaction equation
[F:1][C:2]1([CH2:13]N)[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+].S(=O)(=O)(O)O.[OH2:24]>>[F:1][C:2]1([CH2:13][OH:16])[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[CH:3]1[CH2:11][OH:24]Participants
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, 6.13 g (62.5 mmol) of sulfuric acid was added dropwise over 60 minutes while keeping the inside of the reaction system at 40° C. or less. 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, 7.9 g of 2,3,5,6-tetrafluorobenzenedimethanol was obtained as white crystals. The purity determined from the GC area in percentage was 98.3% and the yield was 73.9%.
Workup
- customInto a 200 ml-volume flask equipped with a thermometer
- temperatureSubsequently, under cooling of the reactor in a water bath
- customat 40° C. or less
- customThe reaction solution obtained
- extractionwas extracted with 10.0 g of methyl ethyl ketone
- washthe organic phase was washed with 5.0 g of an aqueous 5 mass % sulfuric acid solution
- customthe methyl ethyl ketone was removed by distillation, as a result
Sources & evidence
- ORD record
- ord-02e72b8f9eed45aab240839a38b5d509
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06909023B2
Reaction notes
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