Water → 1-Ethoxy-2,3-difluoro-4-(4-vinylcyclohex-1-enyl)benzene

HRID 1787404Notes

Reaction equation

HRID 1787404 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2(O)[CH2:15][CH2:14][CH:13]([CH:16]=[CH2:17])[CH2:12][CH2:11]2)=[C:6]([F:19])[C:5]=1[F:20])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[CH2:17])[CH2:12][CH:11]=2)=[C:6]([F:19])[C:5]=1[F:20])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 575988441-(4-Ethoxy-2,3-difluorophenyl)-4-vinylcyclohexanol

Product 1

HCID 575987621-Ethoxy-2,3-difluoro-4-(4-vinylcyclohex-1-enyl)benzeneYield 14.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Eighth Step: 18.5 g of the compound (17), 0.4 g of p-toluenesulfonic acid and 60 mL of toluene were mixed, and the mixture was refluxed under heating for 1 hour while water distilled out was removed. After cooling the resulting reaction mixture to 25° C., 100 mL of water and 100 mL of toluene were added to and mixed with the reaction mixture. Thereafter, the mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=3/1 by volume) as eluent, and then further purified by recrystallization from ethanol to obtain 2.58 g of 1-ethoxy-2,3-difluoro-4-(4-vinylcyclohex-1-enyl)benzene (No. 12) in white color. The yield based on the compound (16) was 20.2%.

Workup

  1. temperaturethe mixture was refluxed
  2. distillationdistilled out
  3. customwas removed
  4. temperatureAfter cooling
  5. customthe resulting reaction mixture to 25° C.
  6. additionmixed with the reaction mixture
  7. customThereafter, the mixture was separated into an organic layer
  8. extractionextraction to the organic layer
  9. washwashed with a 2N sodium hydroxide aqueous solution
  10. dry with materialby drying over anhydrous magnesium sulfate
  11. customThereafter, the solvent was removed by distillation under reduced pressure
  12. customto obtain a residue
  13. customThe resulting residue was purified by silica gel column chromatography
  14. customfurther purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-bcefbca7a829467ca19117d743d02534
Source dataset
uspto-grants-2009_03
Patent number
US07510749B2

Reaction notes

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