Methyl iodide → HCID 20165433, compound

HRID 256096Notes

Reaction equation

HRID 256096 reaction equation
[CH3:1][CH:2]1[CH:9]2[CH2:10][CH:5]([C:6]([CH3:11])=[CH:7][CH2:8]2)[CH:4]([OH:12])[CH2:3]1.[Na].[CH3:14]I>O1CCCC1>[CH3:14][O:12][CH:4]1[CH2:3][CH:2]([CH3:1])[CH:9]2[CH2:10][CH:5]1[C:6]([CH3:11])=[CH:7][CH2:8]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545Sodium2×HCID 20165425HCID 20165425, compound

Product 1

HCID 20165433HCID 20165433, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 10 g (60.2 mmol) of 4,8-dimethylbicyclo[3.3.1]nona-7-en-2-ol [IA] in 60 ml of tetrahydrofuran were added 1.3 g (56.5 mmol) of sodium and the resulting mixture was heated with stirring at 40° C. After the sodium was dissolved, 12.8 g (90 mmol) of methyl iodide were added dropwise and the resulting mixture was heated with stirring at 40° C. for 10 hours. After cooling, the tetrahydrofuran was distilled off under reduced pressure, the residue was subjected to column chromatography and eluate with toluene gave 7.8 g of the title compound, which had a refrigerant and camphor-like smell.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperaturethe resulting mixture was heated
  3. stirringwith stirring at 40° C. for 10 hours
  4. temperatureAfter cooling
  5. distillationthe tetrahydrofuran was distilled off under reduced pressure

Sources & evidence

ORD record
ord-31877a0d0617427ea4a18832e1cade35
Source dataset
uspto-grants-1987_10
Patent number
US04700008

Reaction notes

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