Methyl iodide → 2-Methylbicyclo[2.2.1]heptan-2-ol

HRID 2211326Notes

Reaction equation

HRID 2211326 reaction equation
[Mg].[CH3:2]I.[CH:4]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][C:5]2=[O:11].[Cl-].[NH4+]>C(OCC)C>[CH3:2][C:5]1([OH:11])[CH2:6][CH:7]2[CH2:10][CH:4]1[CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 2969202-Methylbicyclo[2.2.1]heptan-2-olYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A Grignard reagent was prepared from 96 g (4.0M) of magnesium flakes and 553.0 g (3.9M) of methyl iodide in 600 ml of absolute diethyl ether under a nitrogen gas stream in the conventional manner. 225.0 g (2.05M) of norbornanone (I) (manufactured by Aldrich Chemical Co., Inc.) was added dropwise thereto at room temperature and the resulting mixture was stirred at room temperature over night. The reaction mixture was poured into 800 ml of a saturated aqueous solution of ammonium chloride. The organic phase was collected and dried over anhydrous magnesium sulfate. After evaporation of the ether, the residue was distilled under reduced pressure to give 250.1 g (theoretical yield: 97%) of the aimed compound (II) as a colorless oily material. b.p.: 75° C./18 mmHg.

Workup

  1. customThe organic phase was collected
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter evaporation of the ether
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c9f3ad9b964d4851bbbe75c9495fb9f2
Source dataset
uspto-grants-1995_10
Patent number
US05463118

Reaction notes

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