Water → 4-Oxocyclohexane-1-carbaldehyde
Reaction equation
C1CO[C:3]2([CH2:8][CH2:7][C:6](=[CH:9][O:10]C)[CH2:5][CH2:4]2)[O:2]1.O>C(O)(=O)C>[CH:9]([CH:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]1)=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 10.55 g of 1,1-ethylenedioxy-4-(methoxymethylene)cyclohexane, 130 ml of water and 200 ml of glacial acetic acid was heated to reflux for 1 hour. The solvent was subsequently distilled off on a rotary evaporator and the distillate was extracted twice with methylene chloride. The distillation residue (a yellow oil) was diluted with 200 ml of water, neutralized with sodium carbonate solution and extracted three times with methylene chloride. The organic phases were washed with saturated sodium carbonate solution and the aqueous phases were back-extracted with methylene chloride. The organic phases were dried over magnesium sulphate and evaporated. Distillation of the residual, yellow oil gave 6.7 g (93%) of 4-formylcyclohexanone at 70° C./0.15 Torr.
Workup
- temperaturewas heated
- temperatureto reflux for 1 hour
- distillationThe solvent was subsequently distilled off on a rotary evaporator
- extractionthe distillate was extracted twice with methylene chloride
- additionThe distillation residue (a yellow oil) was diluted with 200 ml of water
- extractionextracted three times with methylene chloride
- washThe organic phases were washed with saturated sodium carbonate solution
- extractionthe aqueous phases were back-extracted with methylene chloride
- dry with materialThe organic phases were dried over magnesium sulphate
- customevaporated
- distillationDistillation of the residual, yellow oil
Sources & evidence
- ORD record
- ord-3feb445cc3524f229a6ab9d1b45098f3
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04676604
Reaction notes
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