Water → HCID 68419193, compound

HRID 1929252Notes

Reaction equation

HRID 1929252 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)(O)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 59609849HCID 59609849, compound

Product 1

HCID 68419193HCID 68419193, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

Procedure

The compound (10) (80.0 g), p-toluenesulfonic acid (2.4 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 obtained was cooled to 30° C., and then water (500 ml) and toluene (900 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and an extractive operation into an organic phase 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 70.3 g of 4-heptyl-1-(3-fluorophenyl)-3-cyclohexene (11). The yield based on the compound (11) was 94.0%.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. customThe reaction mixture obtained
  5. additionmixed
  6. customhad separated into two phases of 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-605d00b8f6284c89824eff3f036fef7f
Source dataset
uspto-grants-2012_05
Patent number
US08187494B2

Reaction notes

Loading…