Isopropanol → 4-Pentylcyclohexanal

HRID 48104

Reaction equation

HRID 48104 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 140856594-PentylcyclohexanalYield 83%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 61850Ruthenium trichlorideSolventHCID 22418719Chloroform waterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ad38f816235d4afa8e8eceaba7c1ce9e
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Linked notes

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