Bromide ion → HCID 54337042, compound
Reaction equation
[Mg].Br[CH2:3][CH:4]([CH3:7])[CH2:5][CH3:6].[Br-].[CH3:9][C:10](=[CH:13][CH2:14][CH3:15])[CH:11]=[O:12].[Cl-].[NH4+]>CCOCC>[CH3:7][CH:4]([CH2:3][CH:11]([OH:12])[C:10]([CH3:9])=[CH:13][CH2:14][CH3:15])[CH2:5][CH3:6]Participants
Conditions
- Temperature
- 10 °C
Procedure
0.72 g (29.8 mg atoms) of magnesium in 3 ml of absolute ether are placed in an apparatus which is customary for Grignard reactions. While stirring there are subsequently added dropwise 5.0 g (33.1 mmol) of 1-bromo-2-methylbutane (90%) in 5 ml of absolute ether so that the ether boils constantly. After completing the addition of the bromide, the mixture is held at reflux temperature for a further 30 minutes, then cooled to 10° C. and a solution of 2.92 g (29.8 mmol) of 2-methyl-2-pentenal in 3 ml of absolute ether is added dropwise. The exothermic reaction causes the temperature to rise to 25° C. After refluxing for a further hour, the reaction product is worked-up with crushed ice and saturated ammonium chloride solution in the customary manner. After separating the aqueous phase, the organic layer is washed with saturated sodium chloride solution, subsequently dried and freed from solvent. The crude product (4.8 g) is distilled and yields 1.74 g of pure 3,6-dimethyl-6-nonen-5-ol (boiling point about 120° C./12 mm Hg; nD20 =1.4560), which has the following spectral data:
Workup
- temperatureat reflux temperature for a further 30 minutes
- customThe exothermic reaction
- customto rise to 25° C
- temperatureAfter refluxing for a further hour
- customAfter separating the aqueous phase
- washthe organic layer is washed with saturated sodium chloride solution
- customsubsequently dried
- distillationThe crude product (4.8 g) is distilled
Sources & evidence
- ORD record
- ord-79f806fe2e874606b1bc46e8a8ad1f1f
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04585662
Reaction notes
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