Potassium Hydroxide → HCID 178444307, compound

HRID 1731453Notes

Reaction equation

HRID 1731453 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].O.NN.[OH-].[K+]>C(O)C.C(O)COCCO>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1)[CH3:19]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 178444316HCID 178444316, compound

Product 1

HCID 178444307HCID 178444307, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 0.9 g of p-[trans-4-(4-pentenyl)cyclohexyl]acetophenone in 8 ml of ethanol and 8 ml of diethylene glycol was treated with 350 ml of hydrazine hydrate while gassing with argon and the solution was then heated to reflux (bath temperature 110° C.) while stirring for 1 hour. Subsequently, the mixture was treated with 421 mg of solid potassium hydroxide, the bath temperature was increased to 210° C. and the ethanol was distilled off. After 3 hours at 210° C. the reaction was interrupted and the mixture was partitioned three times in water/petroleum ether. The organic extracts were washed twice with water, dried over magnesium sulphate and evaporated. Chromatographic separation of the residue (0.85 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 0.76 g (90%) of 4-ethyl-1-[trans-4-(4-pentenyl)cyclohexyl]benzene as a colourless oil; m.p. (C--I) -10.6° C.

Workup

  1. temperaturethe solution was then heated
  2. temperaturethe bath temperature was increased to 210° C.
  3. distillationthe ethanol was distilled off
  4. waitAfter 3 hours at 210° C. the reaction was interrupted
  5. customthe mixture was partitioned three times in water/petroleum ether
  6. washThe organic extracts were washed twice with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customChromatographic separation of the residue (0.85 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record
ord-bfcc38d231184215a050ba35e01bdb6c
Source dataset
uspto-grants-1986_11
Patent number
US04621901

Reaction notes

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