Cyclohexanone → HCID 59602263, compound
Reaction equation
[CH2:1]1[C:5]2(CCCC[C:6]2=[O:11])[CH2:4]CC1.C1(=O)CCCCC1.C[Mg]Cl.[Cl-].[NH4+].[CH3:24][C:25]1([OH:35])[CH2:34][CH2:33][CH2:32][CH2:31][C:26]21[CH2:30][CH2:29][CH2:28][CH2:27]2>O1CCCC1>[C:6]([O:35][C:25]1([CH3:24])[CH2:34][CH2:33][CH2:32][CH2:31][C:26]21[CH2:30][CH2:29][CH2:28][CH2:27]2)(=[O:11])[C:5]([CH3:1])=[CH2:4]Participants
Procedure
With stirring under nitrogen atmosphere at room temperature, a mixture of 100 g of spiro[4.5]decan-6-one (which had been synthesized from cyclohexanone by a method as described in A. P. Krapcho, Synthesis, 1974, p 383 and references cited therein) and 200 ml of tetrahydrofuran was added dropwise to a tetrahydrofuran solution of 1.28 mol methylmagnesium chloride (which had been prepared from 31.1 g of metallic magnesium, 400 ml of tetrahydrofuran and chloromethane), during which time the temperature was kept below 60° C. The reaction mixture was refluxed for 30 minutes, after which a saturated ammonium chloride aqueous solution was added to stop the reaction. Through ordinary work-up of extraction, washing and drying, and subsequent vacuum distillation, there was obtained 93.3 g (yield 87%) of the target compound, 6-methylspiro[4.5]decan-6-ol.
Workup
- customKrapcho, Synthesis, 1974, p 383 and references
- customwas kept below 60° C
- temperatureThe reaction mixture was refluxed for 30 minutes
- customthe reaction
- extractionThrough ordinary work-up of extraction
- washwashing
- customdrying
- distillationsubsequent vacuum distillation
Sources & evidence
- ORD record
- ord-a34d4ad03f034616b05d600c99aa1d0d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791288B2
Reaction notes
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