Bromide ion → Cycloheptanol, 2,2,7,7-tetramethyl-1-(2-propenyl)-
Reaction equation
[Mg].[Br-].C(OCC)C.[CH2:8](Br)[CH:9]=[CH2:10].[CH3:12][C:13]1([CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][C:15]([CH3:21])([CH3:20])[C:14]1=[O:22]>>[CH2:10]([C:14]1([OH:22])[C:15]([CH3:21])([CH3:20])[CH2:16][CH2:17][CH2:18][CH2:19][C:13]1([CH3:23])[CH3:12])[CH:9]=[CH2:8]Participants
Procedure
Magnesium (5.37 g, 0.221 moles) was added to 500 ml four-necked flask equipped with a mechanical stirrer, a dropping funnel, a thermometer, a reflux condenser and a nitrogen gas inlet tube, into which nitrogen gas was passed to remove moisture from the flask. Thereafter, a small amount of a mixed solution of ally bromide (1.5 g, 0.0124 moles)/dried diethyl ether (7.5 ml) was dropped while stirring, followed by dropping a mixed solution of allyl bromide (21.29 g, 0.176 moles)/2,2,7,7-tetramethylcycloheptanone (24.68 g, 0.147 moles)/dried diethyl ether (75 ml) in 2 hours while cooling to 15° C. or below on an iced water bath. The resulting mixture was stirred for 1 hour while keeping at 15° C. or below. Thereafter, the reaction mixture was treated in the same manner as in Example 1, thereby obtaining 23.03 g (yield 74.5%) of the captioned compound. This compound was a colorless transparent liquid having a woody, green, earthy and patchuli oil-like odor.
Workup
- customequipped with a mechanical stirrer, a dropping funnel
- customto remove moisture from the flask
- customin 2 hours
- temperaturewhile cooling to 15° C. or below on an iced water bath
- stirringThe resulting mixture was stirred for 1 hour
- customwhile keeping at 15° C. or below
- additionThereafter, the reaction mixture was treated in the same manner as in Example 1
Sources & evidence
- ORD record
- ord-73bbe037fe46415d8b195d6a89b2cdb5
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04631147
Reaction notes
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