p-Toluenesulfonic acid monohydrate → 1,1-Ethylenedioxy-4-(3,4',5'-trifluorophenyl)-3-cyclohexen

HRID 1769572Notes

Reaction equation

HRID 1769572 reaction equation
[CH2:1]1[CH2:20][O:19][C:3]2([CH2:8][CH2:7][C:6](O)([C:9]3[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[CH:10]=3)[CH2:5][CH2:4]2)[O:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:20]1[CH2:1][O:2][C:3]2([CH2:8][CH2:7][C:6]([C:9]3[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[CH:10]=3)=[CH:5][CH2:4]2)[O:19]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867483998-(3,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 572149021,1-Ethylenedioxy-4-(3,4',5'-trifluorophenyl)-3-cyclohexenYield 65.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,1-Ethylenedioxy-4-hydroxy-4-(3',4',5'-trifluoro-phenyl)cyclohexane (166.2 g) was dissolved in toluene (500 ml), followed by adding p-toluenesulfonic acidmonohydrate (20 g) into the solution, stirring the mixture under reflux for one hour, washing the reaction solution with water (500 ml), drying the organic layer over anhydrous magnesium sulfate, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(3',4',5'-trifluorophenyl)-3-cyclohexene (102.6 g).

Workup

  1. temperatureunder reflux for one hour
  2. washwashing the reaction solution with water (500 ml)
  3. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  4. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-8f6ba38ba29a4fe4bcefc74f2c52acff
Source dataset
uspto-grants-1995_01
Patent number
US05382379

Reaction notes

Loading…