Diethyl Ether → HCID 13782559, compound

HRID 1249330Notes

Reaction equation

HRID 1249330 reaction equation
CI.[CH2:3](OCC)C.[Mg].[CH3:9][C:10]1([CH3:20])[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]1=[O:19]>>[CH3:3][C:11]1([OH:19])[C:12]([CH3:18])([CH3:17])[CH2:13][CH2:14][CH2:15][CH2:16][C:10]1([CH3:20])[CH3:9]

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 132121452,2,7,7-Tetramethylcycloheptan-1-one

Product 1

HCID 13782559HCID 13782559, compoundYield 55.3%

Procedure

A mixed solution of methyl iodide (23.90 g, 0.16 moles)/dried diethyl ether (10 ml) was dropped into a mixture of magnesium (2.90 g, 0.12 moles)/dried diethyl ether (20 ml) in 1 hour while stirring under water-cooling conditions. The mixture was stirred for 48 hours at room temperature and subjected to separation by filtration. Into the resulting filtrate was dropped a mixed solution of 2,2,7,7-tetramethylcycloheptanone (16.80 g, 0.10 mole)/dried diethyl ether (30 ml) in 30 minutes while stirring at room temperature. The mixture was stirred at room temperature for 48 hours. The resulting reaction mixture was treated in the same manner as in Example 1 to obtain 10.20 g (yield 55.3%) of the captioned compound. This compound was a white solid having a woody, earthy camphoraceous and patchuli oil-like odor.

Workup

  1. temperaturecooling conditions
  2. stirringThe mixture was stirred for 48 hours at room temperature
  3. customsubjected to separation by filtration
  4. stirringwhile stirring at room temperature
  5. stirringThe mixture was stirred at room temperature for 48 hours
  6. customThe resulting reaction mixture
  7. additionwas treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-aa9d3377a72a47d1ae622634809eada4
Source dataset
uspto-grants-1986_12
Patent number
US04631147

Reaction notes

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