Toluene → HCID 19107881, compound

HRID 1929263Notes

Reaction equation

HRID 1929263 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 (47) (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, and mixed thereto. The mixture was allowed to stand until it had separated into 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 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 (48). The compound (48) obtained was a colorless oil, having the boiling point at 131° C./3 mmHg 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 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-6534ad8daee94f52a17d3a11a91ceecc
Source dataset
uspto-grants-2012_05
Patent number
US08187494B2

Reaction notes

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