Toluene → 5-Isopropyl-1,3-dimethyl-bicyclo[3.2.1]oct-3-en-2-one
Reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH2:8][CH:9]=C(C)C)[CH2:5][CH2:6][CH:7]=1.C([Al](Cl)Cl)C.[NH4+].[Cl-].[C:22]1(C)[CH:27]=CC=C[CH:23]=1>>[CH:22]([C:6]12[CH2:5][C:4]([CH3:13])([CH2:8][CH2:9]1)[C:3](=[O:14])[C:2]([CH3:1])=[CH:7]2)([CH3:27])[CH3:23]Participants
5
Procedure
To a solution of 2,6-dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26.04 mmol) in toluene (40 ml) was added dropwise neat EtAlCl2 (97%, 1.5 eq., 4.96 g, 39.06 mmol). During the addition, the temperature was kept below 10° C. The brown mixture was kept at room temperature over night and was then poured on icecold saturated NH4Cl. The mixture was extracted with MTBE, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled bulb to bulb to yield 4.50 g (90%) of an colorless oil.
Workup
- additionDuring the addition
- customwas kept below 10° C
- waitThe brown mixture was kept at room temperature over night
- extractionThe mixture was extracted with MTBE
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- distillationThe residue was distilled bulb to bulb
Sources & evidence
- ORD record
- ord-46c8f7c24d3c44b4b8e49d55ad04b40d
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691802B2
Reaction notes
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