Hydrochloric Acid → 2,3,5,6-Tetrafluorobenzenedimethanol

HRID 1665904Notes

Reaction equation

HRID 1665904 reaction equation
[BH4-].[Na+].[CH2:3](COC)[O:4]C.[F:9][C:10]1[C:18]([F:19])=[C:17](C(O)=O)[C:16]([F:23])=[C:15]([F:24])[C:11]=1[C:12]([OH:14])=O.Cl>O.C1(C)C=CC=CC=1>[F:24][C:15]1([CH2:3][OH:4])[C:16]([F:23])=[CH:17][C:18]([F:19])=[C:10]([F:9])[CH:11]1[CH2:12][OH:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80711,2-Dimethoxyethane2×HCID 695492,3,5,6-Tetrafluoroterephthalic acidHCID 4311764Sodium borohydride

Product 1

HCID 667129532,3,5,6-TetrafluorobenzenedimethanolYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Into a 200 mL flask equipped with a reflux condenser, 2.58 g of sodium borohydride and 25 g of dimethoxyethane were charged. The obtained mixture was adjusted to 50° C. and then, a solution obtained by mixing 6.10 g of 2,3,5,6-tetrafluoroterephthalic acid with 20 g of dimethoxyethane was added dropwise thereto over 1 hour while stirring. The obtained mixture was stirred for 7 hours at 60° C. To the obtained reaction mixture, 20 g of toluene was added followed by cooling to 50° C. Eight point five grams of 35% by weight hydrochloric acid was added dropwise thereto over 1 hour to stir at 60° C. for 6 hours. To the obtained mixture, 30 g of water was added followed by separating to an organic layer and an aqueous layer. The aqueous layer was extracted twice with 30 g of ethyl acetate. The obtained organic layers were mixed and washed with 10 g of a saturated aqueous potassium carbonate solution and then with 10 g of water. The organic layer was concentrated and the obtained solids were recrystallized with toluene and hexane to obtain white powder crystals of 2,3,5,6-tetrafluorobenzenedimethanol. The crystals were analyzed by liquid chromatography absolute calibration curve method to find out that the purity thereof was 95.1%. Yield: 95%.

Workup

  1. customInto a 200 mL flask equipped with a reflux condenser
  2. customwas adjusted to 50° C.
  3. customa solution obtained
  4. additionwas added dropwise
  5. stirringThe obtained mixture was stirred for 7 hours at 60° C
  6. additionwas added
  7. stirringover 1 hour to stir at 60° C. for 6 hours
  8. customby separating to an organic layer
  9. extractionThe aqueous layer was extracted twice with 30 g of ethyl acetate
  10. additionThe obtained organic layers were mixed
  11. washwashed with 10 g of a saturated aqueous potassium carbonate solution
  12. concentrationThe organic layer was concentrated
  13. customthe obtained solids were recrystallized with toluene and hexane

Sources & evidence

ORD record
ord-1b1d6459cb954e259658d4ae3bb83faa
Source dataset
uspto-grants-2011_10
Patent number
US08039680B2

Reaction notes

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