Acetic Acid → 4-Oxocyclohexane-1-carbaldehyde

HRID 247677Notes

Reaction equation

HRID 247677 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.C(O)(=O)C>O>[CH:9]([CH:6]1[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]1)=[O:10]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 552771378-(Methoxymethylene)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 111709734-Oxocyclohexane-1-carbaldehydeYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 28.2 g of 1,1-ethylenedioxy-4-(methoxymethylene)cyclohexane, 770 ml of glacial acetic acid and 385 ml of water was heated to reflux for 1 hour in a round flask while gassing with nitrogen. Thereafter, the yellowish clear solution was cooled to room temperature, diluted with 800 ml of water and extracted three times with 700 ml of methylene chloride each time. The organic phases were washed twice with 500 ml of 10% (wt./vol.) sodium carbonate solution each time, dried over sodium sulphate, filtered and concentrated. Chromatographic separation of the brownish liquid obtained (18.5 g) on silica gel with methylene chloride as the eluent finally gave 16.7 g of 4-formylcyclohexanone as a brownish liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour in a round flask
  3. extractionextracted three times with 700 ml of methylene chloride each time
  4. washThe organic phases were washed twice with 500 ml of 10% (wt./vol.) sodium carbonate solution each time
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatographic separation of the brownish liquid

Sources & evidence

ORD record
ord-20291a54134a4fe5b3e068427ca3e505
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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