Toluene → 4-Pentyl-(2,3-difluorophenyl)-cyclohexene

HRID 1943543Notes

Reaction equation

HRID 1943543 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])(O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 596098104-Pentyl(2,3-difluorophenyl)cyclohexanol

Product 1

HCID 144956434-Pentyl-(2,3-difluorophenyl)-cyclohexeneYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

The compound (8) (215.1 g), p-toluenesulfonic acid (6.5 g) and toluene (500 ml) were mixed, and the mixture was heated under reflux for 2 hours while water being distilled was removed. The reaction mixture was cooled to 30° C., and then water (500 ml) and toluene (500 ml) were added thereto and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The product obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder, and dried, giving 186.6 g of 4-pentyl-(2,3-difluorophenyl)-cyclohexene (9). The yield based on the compound (8) was 92.7%.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. additionwater (500 ml) and toluene (500 ml) were added
  5. additionmixed
  6. customhad separated into two phases of organic and
  7. extractionaqueous phases, and extraction into an organic phase
  8. customThe organic phase obtained
  9. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe product obtained
  12. customwas purified with a fractional operation by means of column chromatography
  13. customdried

Sources & evidence

ORD record
ord-12958e737329424c8949daf079cd9322
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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