Water → 1-Bromo-4-(4-propylcyclohexa-1-enyl)benzene

HRID 641101Notes

Reaction equation

HRID 641101 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 592571391-(4-Bromophenyl)-4-propylcyclohexanol

Product 1

HCID 543121671-Bromo-4-(4-propylcyclohexa-1-enyl)benzeneYield 57.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

50.1 g of the compound (15), 0.5 g of p-toluenesulfonic acid and 200 mL of toluene were mixed, and the mixture was refluxed under heating for 3 hours while water distilled out was removed. After cooling the resulting reaction mixture to 30° C., 200 mL of water and 100 mL of toluene were added to and mixed with the reaction mixture, which was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using heptane as eluent, and then further purified by recrystallization from Solmix A-11 to obtain 27.2 g of 1-bromo-4-(4-propylcyclohexa-1-enyl)benzene (16).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationdistilled out
  3. customwas removed
  4. temperatureAfter cooling
  5. customthe resulting reaction mixture to 30° C.
  6. additionmixed with the reaction mixture, which
  7. customwas separated into an organic layer
  8. extractionextraction to the organic layer
  9. washwashed with a 2N sodium hydroxide aqueous solution
  10. dry with materialby drying over anhydrous magnesium sulfate
  11. customThereafter, the solvent was removed by distillation under reduced pressure
  12. customto obtain a residue
  13. customThe resulting residue was purified by silica gel column chromatography
  14. customfurther purified by recrystallization from Solmix A-11

Sources & evidence

ORD record
ord-188b2529ed43404ab21bd49dc64b2980
Source dataset
uspto-grants-2010_04
Patent number
US07695777B2

Reaction notes

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