Isopropenyl acetate → 2-(2-Oxopropyl)cyclohexanone
Reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].C([O:22][C:23]([CH3:25])=[CH2:24])(=O)C.[C:26]1(=[O:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(O)(=O)C.O>[CH2:24]([CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][C:26]1=[O:32])[C:23]([CH3:25])=[O:22]Participants
8
Conditions
- Temperature
- 70 °C
Procedure
To a solution of manganic acetate in acetic acid, prepared in situ by the addition of 16 g. of potassium permanganate (0.1 m.) to 88 g. of manganous acetate dihydrate (Mn(OAc)2.2H2O) (0.42 m.) in 570 milliliters of glacial acetic acid followed by 124 ml. of acetic anhydride and 60 g. of potassium acetate, were added 100 g. (1.0 m.) of isopropenyl acetate and 98 g. (1.0 m.) of cyclohexanone. The reaction mixture was heated under nitrogen to 70° C. until the brown manganic color disappeared. The reaction mixture was cooled, diluted with water, and extracted with ether. The product, 2-acetonyl-cyclohexanone ##STR78## was isolated by distillation, b.p. 70° C. at .05 mm. mercury, yield about 8 g. (20% based on Mn).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with ether
Sources & evidence
- ORD record
- ord-cfe02e3ada2d4203b7a21df9b6adee2c
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04119646
Reaction notes
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