HCID 20165433, compound → 2-Methoxynonane

HRID 256097Notes

Reaction equation

HRID 256097 reaction equation
[CH3:1][O:2][CH:3]1[CH2:10][CH:9]([CH3:11])[CH:8]2C[CH:4]1[C:5](C)=[CH:6][CH2:7]2.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 20165433HCID 20165433, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 126397612-MethoxynonaneYield 107.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1 g (5.6 mmol) of 4,8-dimethylbicyclo[3.3.1]nona-7-en-2-yl methyl ether [IB] in 10 ml of ethanol was added 0.1 g of 5% of Pd/C and the resulting mixture was heated with stirring at a hydrogen pressure of 20 atm and a reaction temperature of 70° C. for 6 hours. After cooling, the Pd/C was filtered off and the ethanol was distilled off under reduced pressure. The residue was subjected to column chromatography and eluate with toluene gave 0.95 g of the title compound, which had a camphor-like smell.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureAfter cooling
  3. filtrationthe Pd/C was filtered off
  4. distillationthe ethanol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7aa791a10ffb468b9abbd7e28b62249a
Source dataset
uspto-grants-1987_10
Patent number
US04700008

Reaction notes

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