Reaction equation
C[Mg]I.[Mg].[CH3:5]I.[CH3:7][CH:8]([CH:11]=[CH:12][CH:13]1[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][CH:15]=[C:14]1[CH3:21])[CH:9]=[O:10]>CCOCC>[CH3:7][CH:8]([CH:11]=[CH:12][CH:13]1[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][CH:15]=[C:14]1[CH3:21])[CH:9]([OH:10])[CH3:5]Participants
Conditions
- Temperature
- 30 °C
Procedure
A solution of methylmagnesium iodide, prepared from 11 g of magnesium shavings and 76 g of methyl iodide, in 700 ml of absolute ether is added dropwise at -10° C under nitrogen to a solution of 62 g of 2-methyl-4-(2,6,6-trimethyl-2-cyclohexenyl)-3-butenal in 700 ml of ether. The mixture is stirred for 4 hours at 30° C and then poured on to an excess of ice-cold ammonium chloride solution. The mixture is extracted with ether in the usual manner, the extract is washed neutral with water and dried over anhydrous sodium sulphate to give, after removal of the solvent, 66 g of a yellow, slightly viscous oil which, after distillation in vacuo, yields 52 g of 3-methyl-5-(2,6,6-trimethyl-2-cyclohexenyl)-4-penten-2-ol; b.p.0.008 = 90°; nD20 = 1.4890. This alcohol has a very fine, tenacious sandalwood odour.
Workup
- additionpoured on to an excess of ice-cold ammonium chloride solution
- extractionThe mixture is extracted with ether in the usual manner
- washthe extract is washed neutral with water
- dry with materialdried over anhydrous sodium sulphate
- customto give
- customafter removal of the solvent, 66 g of a yellow, slightly viscous oil which
- distillationafter distillation in vacuo
Sources & evidence
- ORD record
- ord-35099c29f81041858d667a295bee130f
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04010213
Linked notes
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