Ethyl Bromide → HCID 13782560, compound

HRID 1249331Notes

Reaction equation

HRID 1249331 reaction equation
[CH2:1](Br)[CH3:2].[Li].[CH3:5][C:6]1([CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([CH3:14])([CH3:13])[C:7]1=[O:15]>C(OCC)C>[CH2:1]([C:7]1([OH:15])[C:8]([CH3:14])([CH3:13])[CH2:9][CH2:10][CH2:11][CH2:12][C:6]1([CH3:16])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 3028194LithiumHCID 132121452,2,7,7-Tetramethylcycloheptan-1-one

Product 1

HCID 13782560HCID 13782560, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Conditions

Temperature
-30 °C

Procedure

A mixed solution of ethyl bromide (33.30 g, 0.40 moles)/dried diethyl ether (40 ml) was dropped into a mixture of lithium (4.30 g, 0.62 moles)/dried diethyl ether (25 ml) in 2 hours while stirring at -30° C., followed by further adding dried diethyl ether (40 ml) and raising the temperature to 0° C. The mixture was subjected to separation by filtration. The resulting filtrate was dropped into a mixed solution of 2,2,7,7-tetramethylcycloheptanone (15.00 g, 0.09 moles)/dried diethyl ether (40 ml) in 30 minutes while stirring at 0° C. The mixture was stirred at 0° C. for 2 hours. The resulting reaction mixture was treated in the same manner as in Example 1 to obtain 13.50 g (yield 76.4%) of the captioned compound. This compound was a colorless transparent liquid having a woody, earthy and patchuli oil-like odor.

Workup

  1. temperatureraising the temperature to 0° C
  2. customThe mixture was subjected to separation by filtration
  3. stirringwhile stirring at 0° C
  4. stirringThe mixture was stirred at 0° C. for 2 hours
  5. customThe resulting reaction mixture
  6. additionwas treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-3f1f0f61f78b404786c8092515adcb71
Source dataset
uspto-grants-1986_12
Patent number
US04631147

Reaction notes

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