Hydrochloric Acid → 4-[4-(4-Pentylbicyclo[2.2.2]octyl)phenyl]cyclohexanone

HRID 635134

反応式

HRID 635134 の反応式
Br[C:2]12[CH2:9][CH2:8][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[C:15]1([CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>[N+](C1C=CC=CC=1)([O-])=O.ClCCl.[Fe](Cl)(Cl)Cl>[CH2:10]([C:5]12[CH2:8][CH2:9][C:2]([C:18]3[CH:19]=[CH:20][C:15]([CH:21]4[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]4)=[CH:16][CH:17]=3)([CH2:3][CH2:4]1)[CH2:7][CH2:6]2)[CH2:11][CH2:12][CH2:13][CH3:14]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 786054-PhenylcyclohexanoneHCID 125349771-Bromo-4-pentylbicyclo[2.2.2]octane

生成物 1

HCID 212577934-[4-(4-Pentylbicyclo[2.2.2]octyl)phenyl]cyclohexanone収率 69%

試薬・触媒・溶媒 3

HCID 24380Iron chloride (FeCl3)触媒HCID 6344Dichloromethane溶媒HCID 7416Nitrobenzene溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 1-bromo-4-pentylbicyclo[2.2.2]octane (6 g, 23 mmol) in sieve-dried nitrobenzene (100 cm3) is added dropwise to a stirred solution of 4-phenylcyclohexanone (3.9 g, 23 mmol) and anhydrous iron(III)chloride (1.2 g, 9 mmol) in sieve-dried nitrobenzene (100 cm3) maintained at 80° C. through the addition and overnight. The cooled solution is added to a small volume of hydrochloric acid and stirred for 20 min. The organic layer is separated off and steam-distilled to yield a solid residue. This is taken up in dichloromethane and dried (MgSO4). The raw product is crystallised from ethanol to yield the desired 4-[4-(4-pentylbicyclo[2.2.2]octyl)phenyl]cyclohexanone (5.4 g, 69%).

後処理

  1. customThe organic layer is separated off
  2. distillationsteam-distilled
  3. customto yield a solid residue
  4. dry with materialdried (MgSO4)
  5. customThe raw product is crystallised from ethanol

出典と根拠

ORDレコード
ord-be735ef3d5cf49dcaf2d6850a47c7c20
出典データセット
uspto-grants-2001_02
特許番号
US06187393B1

関連ノート

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