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

HRID 1734391ノート

反応式

HRID 1734391 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 572433252-(4-Trifluoromethyloxyphenyl)ethyl-4-(4-pentylcyclohexyl)cyclohexanol収率 120.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
90 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-96a26ae812ad40b2990ee6846406bca0
出典データセット
uspto-grants-1996_07
特許番号
US05534187

反応ノート

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