Ethanol → HCID 12893797, compound

HRID 1156366Notes

Reaction equation

HRID 1156366 reaction equation
[CH2:1]([C:5]([CH:7]1[CH2:12][CH2:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH2:8]1)=[O:6])[CH:2]([CH3:4])[CH3:3].[CH2:15]([OH:17])C.C=O.[OH-].[K+]>CO.C(O)(=O)C>[CH2:1]([C:5]([C:7]1([CH2:15][OH:17])[CH2:12][CH2:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH2:8]1)=[O:6])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 12893794HCID 12893794, compound

Product 1

HCID 12893797HCID 12893797, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 65.6 g (0.338 mole) of 3,4-dimethylcyclohex-3-enyl isobutyl ketone (Example XXII), 120 ml of ethanol and 109.6 g of 37% strength formaldehyde solution (=1.35 moles) is brought to a pH of 11-12 with a 15% strength solution of potassium hydroxide in methanol, and is then refluxed for 44 hours, the pH being checked. Thereafter the solution is brought to pH 5 with glacial acetic acid and the solvent is distilled off under reduced pressure. Water is added to the residue and after saturation with sodium chloride the mixture is extracted five times with toluene. The organic phases are dried over anhydrous sodium sulfate, the solvent is distilled off on a rotary evaporator and the residue is distilled under reduced pressure. 37.7 g of 3,4-dimethyl-1-hydroxy-methyl-cyclohex-3-enyl isobutyl ketone pass over at 112°-116° C./0.1 mm Hg.

Workup

  1. temperatureis then refluxed for 44 hours
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionWater is added to the residue
  4. extractionafter saturation with sodium chloride the mixture is extracted five times with toluene
  5. dry with materialThe organic phases are dried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off on a rotary evaporator
  7. distillationthe residue is distilled under reduced pressure
  8. customover at 112°-116° C./0.1 mm Hg

Sources & evidence

ORD record
ord-1f2da44f565d479499cc584d3c9dced4
Source dataset
uspto-grants-1982_06
Patent number
US04335138

Reaction notes

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