Water → 4-Oxocyclohexane-1-carbaldehyde

HRID 2254952Notes

Reaction equation

HRID 2254952 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

4

Reactant 2

HCID 962WaterHCID 552771378-(Methoxymethylene)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 111709734-Oxocyclohexane-1-carbaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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, at 70° C./0.15 Torr, 6.7 g (93%) of 4-formylcyclohexanone.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. distillationThe solvent was subsequently distilled off on a rotary evaporator
  4. extractionthe distillate was extracted twice with methylene chloride
  5. additionThe distillation residue (a yellow oil) was diluted with 200 ml of water
  6. extractionextracted three times with methylene chloride
  7. washThe organic phases were washed with saturated sodium carbonate solution
  8. extractionthe aqueous phases were back-extracted with methylene chloride
  9. dry with materialThe organic phases were dried over magnesium sulphate
  10. customevaporated
  11. distillationDistillation of the residual, yellow oil

Sources & evidence

ORD record
ord-c237b2368f684628bd54010c7536790c
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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