Toluene → HCID 19107881, compound

HRID 1943549Notes

Reaction equation

HRID 1943549 reaction equation
[CH2:1]([O:5][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][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([O:5][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][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 59609814HCID 59609814, compound

Product 1

HCID 19107881HCID 19107881, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

The compound (23) (130.1 g), p-toluenesulfonic acid (1.3 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 solution obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder, and dried, giving 71.6 g of 4-butoxy-(2,3-difluorophenyl)cyclohexene (24). The compound (24) obtained was a colorless oil, having the boiling point at 131 to 132° C./3 mmHg, and the yield based on the compound (6) was 66.5%.

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 solution obtained
  12. customwas purified with a fractional operation by means of column chromatography
  13. customdried

Sources & evidence

ORD record
ord-3acdad4188b843c0b59b48f2cfa2c32d
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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