Ammonium Chloride → 2-(4-Trifluoromethyloxyphenyl)ethyl-4-(4-pentylcyclohexyl)cyclohexanol

HRID 1378882Notes

Reaction equation

HRID 1378882 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11]Br)=[CH:6][CH:5]=1.FC(F)(F)C1C=CC(Br)=CC=1.FC(F)(F)OC1C=CC(Br)=CC=1.[CH2:38]([CH:43]1[CH2:48][CH2:47][CH:46]([CH:49]2[CH2:54][CH2:53][C:52](=[O:55])[CH2:51][CH2:50]2)[CH2:45][CH2:44]1)[CH2:39][CH2:40][CH2:41][CH3:42].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:52]2([OH:55])[CH2:51][CH2:50][CH:49]([CH:46]3[CH2:47][CH2:48][CH:43]([CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:44][CH2:45]3)[CH2:54][CH2:53]2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 113571624'-Pentyl[1,1'-bi(cyclohexane)]-4-oneHCID 153901221-(2-Bromoethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 572433252-(4-Trifluoromethyloxyphenyl)ethyl-4-(4-pentylcyclohexyl)cyclohexanolYield 120.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(4-trifluoromethyloxyphenyl)ethyl bromide (10.0 g, 0.037 mol) prepared in the same manner as in Example 1 except that 4-trifluoromethylbromobenzene was replaced by 4-trifluoromethyloxybromobenzene, with THF (50 ml), was heated at 90° C. for 40 minutes in a sealed tube reactor, to obtain a yellow, uniform solution, followed by adding this solution to a THF (40 ml) solution of 4-(4-pentylcyclohexyl)cyclohexanone (9.27 g, 0.037 mol), stirring the mixture at room temperature for 2 hours, feeding the reaction substance into a saturated aqueous solution of NH4Cl, twice extracting with ethyl acetate (50 ml), washing the resulting organic layer with an aqueous solution of NaCl, drying over anhydrous MgSO4, removing the anhydrous MgSO4, distilling off the solvent under reduced pressure, to obtain a pale yellow, oily 1-(2-(4-trifluoromethyloxyphenyl)ethyl-4-(4-pentylcyclohexyl)cyclohexanol (19.7 g), adding thereto toluene (50 ml) and Amberlyst (0.9 g), heating the mixture under reflux for one hour, while removing formed water, allowing the resulting substance to cool, feeding it to a saturated aqueous solution of NH4Cl, twice washing the separated organic layer with water, drying over anhydrous MgSO4, filtering off the anhydrous MgSO4, distilling off the solvent under reduced pressure, subjecting the residue to column chromatography (silica gel, eluent: heptane) and twice recrystallizing from a mixed solvent of ethanol (10 ml) with benzene (1 ml), to obtain 1-(2-(4-trifluoromethyloxyphenyl)ethyl)-4-(4-pentylcyclohexyl)cyclohexene (1.0 g). Yield: 6%.

Workup

  1. customto obtain a yellow, uniform solution
  2. extractiontwice extracting with ethyl acetate (50 ml)
  3. washwashing the resulting organic layer with an aqueous solution of NaCl
  4. dry with materialdrying over anhydrous MgSO4
  5. customremoving the anhydrous MgSO4
  6. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-46f0ea0724db4051bef34bf333fd129c
Source dataset
uspto-grants-1997_09
Patent number
US05670085

Reaction notes

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