Potassium Hydroxide → 4-methyl-4-phenylcyclohexanone

HRID 1576211Notes

Reaction equation

HRID 1576211 reaction equation
[CH:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=O.O.NN.[OH-].[K+]>C(O)CO>[CH3:1][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21433608HCID 21433608, compound2×

Product 1

HCID 122302774-methyl-4-phenylcyclohexanoneYield 67%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 9.3 g. (0.038 mole) of 4-formyl-4-phenyl cyclohexanone, ethylene ketal (prepared in Example 30), 5 ml. of hydrazine hydrate and 6.4 g. of potassium hydroxide in 120 ml. of ethylene glycol is heated at reflux for about 1 hour. The solvent is then allowed to distill until the pot temperature comes to about 200°C. After about 5 hours the mixture is allowed to cool and then diluted with water and brine and evaporated to dryness. The residue is chromatographed on 750 ml. of Florisil (magnesium silicate) with elution by 1% ethyl acetate in Skellysolve B. The crystalline fractions are combined and recrystallized from a mixture of methanol and water to give 5.92 g. (67% yield) of 4-methyl-4-phenylcyclohexanone, ethylene ketal, having a melting point of 48° to 50°C.

Workup

  1. additionA mixture of 9.3 g
  2. temperatureat reflux for about 1 hour
  3. distillationto distill until the pot temperature
  4. customcomes to about 200°C
  5. temperatureto cool
  6. additiondiluted with water and brine
  7. customevaporated to dryness
  8. customThe residue is chromatographed on 750 ml
  9. washof Florisil (magnesium silicate) with elution by 1% ethyl acetate in Skellysolve B
  10. customrecrystallized from a mixture of methanol and water
  11. customto give 5.92 g

Sources & evidence

ORD record
ord-b2206c7e3399471e81cacf329794855b
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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