Toluene → 4-Propyl-1-(3-fluorophenyl)-3-cyclohexene

HRID 1929255Notes

Reaction equation

HRID 1929255 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)(O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([C:4]1[CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 549193644-Propyl-1-(3-fluorophenyl)-cyclohexanol

Product 1

HCID 684192424-Propyl-1-(3-fluorophenyl)-3-cyclohexeneYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

The compound (18) (13.5 g), p-toluenesulfonic acid (0.4 g) and toluene (250 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 (300 ml) and toluene (500 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution 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 7.7 g of 4-propyl-1-(3-fluorophenyl)-3-cyclohexene (19). The yield based on the compound (18) was 61.7%.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. additionwater (300 ml) and toluene (500 ml) were added
  5. additionmixed
  6. customhad separated into organic and aqueous phases
  7. customThe organic phase obtained
  8. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solution obtained
  11. customwas purified with a fractional operation by means of column chromatography
  12. customdried

Sources & evidence

ORD record
ord-8f59c07c06ab464cadbaaf71ca279641
Source dataset
uspto-grants-2012_05
Patent number
US08187494B2

Reaction notes

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