Water → 1-(4-Ethoxy-2,3-difluorophenyl)-4-(4-butoxy-2,3-difluorophenyl)cyclohexene

HRID 1511488Notes

Reaction equation

HRID 1511488 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]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:18]([F:27])[C:17]=3[F:28])[CH2:12][CH2:11]2)=[C:6]([F:30])[C:5]=1[F:31])[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]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:18]([F:27])[C:17]=3[F:28])[CH2:12][CH:11]=2)=[C:6]([F:30])[C:5]=1[F:31])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 669627671-(4-Ethoxy-2,3-difluorophenyl)-4-(4-butoxy-2,3-difluorophenyl)cyclohexan-1-ol

Product 1

HCID 669625531-(4-Ethoxy-2,3-difluorophenyl)-4-(4-butoxy-2,3-difluorophenyl)cyclohexeneYield 56.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

Procedure

The compound (29) (19.0 g), p-toluenesulfonic acid (0.57 g) and toluene (200 ml) were mixed, and the mixture was heated under reflux for 2 hours while water being distilled was removed. The obtained reaction mixture was cooled to 30° C., and water (200 ml) and toluene (200 ml) were added thereto, and mixed. The mixture was then allowed to separate into organic and aqueous phases, and the extraction into an organic phase was carried out. The organic phase obtained was washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The solution obtained was purified by means of column chromatography (silica gel; toluene), and further purified by means of recrystallization (Solmix A-11: ethyl acetate=2:1 by volume), giving 10.3 g of 1-(4-ethoxy-2,3-difluorophenyl)-4-(4-butoxy-2,3-difluorophenyl)cyclohexene (No. 77). The yield based on the compound (27) was 55.0%.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. customThe obtained reaction mixture
  5. additionmixed
  6. customto separate into organic and aqueous phases
  7. extractionthe extraction into an organic phase
  8. customThe organic phase obtained
  9. washwas washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solution obtained
  12. customwas purified by means of column chromatography (silica gel; toluene)
  13. customfurther purified by means of recrystallization (Solmix A-11: ethyl acetate=2:1 by volume)

Sources & evidence

ORD record
ord-e02cc2f1953843629a349899d7edbb86
Source dataset
uspto-grants-2012_07
Patent number
US08216489B2

Reaction notes

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