Isopropanol → Cyclooctane

HRID 2253952Notes

Reaction equation

HRID 2253952 reaction equation
[CH:1]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.CC(O)C>O.[N+]([O-])([O-])=O.[Ni+2].[N+]([O-])([O-])=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Rh].[Rh].[Rh].[Rh].CC(C)=O>[CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 2

HCID 3776IsopropanolHCID 8135cis,cis-1,5-Cyclooctadiene

Product 2

HCID 9266CyclooctaneHCID 136091-Cyclooctene

Reagents, catalysts & solvents 3

HCID 994031219584-30-6CatalystHCID 23169391HCID 23169391, compoundCatalystHCID 180AcetoneSolvent

Procedure

0.3 ml of 1,5-cyclooctadiene, 32 ml of 2-propanol, 8 ml of acetone, 2.2 mg of nickel nitrate hydrate and 3 mg of tetrarhodiumdodecacarbonyl [Rh4 (CO)12 ] were fed into the same quartz cell as that used in the Example 1. Nitrogen gas was bubbled through the contents under stirring for 10 minutes and thereafter, the irradiation of the cell with light was started. The stirring was conducted with a magnetic stirrer. The reaction cell was put in a quartz-window thermostatic chamber to keep the reaction temperature at 20° C. The rays which were emitted from a 500-W high-pressure mercury lamp set on an irradiation apparatus as an outer light source and passed through a filter UV-25, mfd. by Toshiba Corporation, were used in the irradiation. After the irradiation had been conducted for 5 hours in such a manner, the reaction solution was analyzed by gas chromatography. Cyclooctene was obtained in a yield of 93% with the formation cyclooctane in a yield of 3%. 4% of unreacted 1,5-cyclooctadiene remained.

Workup

  1. customNitrogen gas was bubbled through the contents
  2. customthe irradiation of the cell with light
  3. customThe stirring was conducted with a magnetic stirrer
  4. customat 20° C
  5. customby Toshiba Corporation, were used in the irradiation
  6. customAfter the irradiation
  7. waithad been conducted for 5 hours

Sources & evidence

ORD record
ord-027c9d703c6c472f8c74d12c0df4523b
Source dataset
uspto-grants-1993_08
Patent number
US05233110

Reaction notes

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