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

HRID 1378882노트

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HRID 1378882 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
90 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-46f0ea0724db4051bef34bf333fd129c
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670085

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