Isopropanol → 4-Pentylcyclohexanal

HRID 48104

반응식

HRID 48104 반응식
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].I([O-])(=O)(=O)=O.[Na+].CC(O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[CH2:1]([CH:6]1[CH2:7][CH2:8][CH:9]([CH:12]=[O:13])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 13548135(4-Pentylcyclohexyl)methanolHCID 23667635Sodium periodate

생성물 1

HCID 140856594-Pentylcyclohexanal수율 83%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 61850Ruthenium trichloride용매HCID 22418719Chloroform water용매

실험 절차

To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%).

후처리

  1. stirringthe reaction mixture was stirred for another 30 min at 60 C
  2. filtrationfiltered through celite
  3. extractionextracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (dichloromethane)

출처 및 근거

ORD 기록
ord-ad38f816235d4afa8e8eceaba7c1ce9e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703082B1

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