p-Toluenesulfonic acid monohydrate → beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilyl styrene

HRID 1174446

Reaction equation

HRID 1174446 reaction equation
O[CH:2]([C:19]1[CH:24]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29][CH2:30][CH3:31])=[C:21]([F:32])[C:20]=1[C:33]([F:36])([F:35])[F:34])[CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[Na]>C1(C)C=CC=CC=1>[CH2:16]([CH:13]1[CH2:12][CH2:11][CH:10]([CH:7]2[CH2:6][CH2:5][CH:4]([CH:3]=[CH:2][C:19]3[CH:24]=[C:23]([Si:25]([CH3:27])([CH3:26])[CH3:28])[C:22]([O:29][CH2:30][CH3:31])=[C:21]([F:32])[C:20]=3[C:33]([F:35])([F:36])[F:34])[CH2:9][CH2:8]2)[CH2:15][CH2:14]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 231596831-Hydroxy-1-(2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilylphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethaneHCID 23872008Sodium hydrochloride

Product 1

HCID 86614748beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilyl styreneYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.7 g of the crude 1-hydroxy-1-(2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilylphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane obtained in the first step was dissolved in toluene. 0.68 g (3.57 mmol) of p-toluene sulfonic acid monohydrate was added and refluxed under heating for 2 hours while dewatering by using a Dean Stark apparatus. The reaction mixture was poured into 200 ml of an aqueous sodium hydrogen chloride solution and extracted with 200 ml of toluene. The organic layer was washed with 200 ml of water and then with 100 ml of an aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate, it was concentrated under a reduced pressure to obtain 16.03 g of a crude β-(4-(4-propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilyl styrene.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. extractionextracted with 200 ml of toluene
  4. washThe organic layer was washed with 200 ml of water
  5. dry with materialwith 100 ml of an aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate, it
  6. concentrationwas concentrated under a reduced pressure

Sources & evidence

ORD record
ord-5962d41c4bad41de9d6b8599510dc3b1
Source dataset
uspto-grants-2010_11
Patent number
US07838087B2

Linked notes

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