Potassium Hydroxide → HCID 178444308, compound

HRID 1285073Notes

Reaction equation

HRID 1285073 reaction equation
[CH: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)=[CH:2]\[CH2:3][CH2:4][CH3:5].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](/[CH:1]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1)[CH3:19]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 178444317HCID 178444317, compound

Product 1

HCID 178444308HCID 178444308, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1.35 g of p-[trans-4-(trans-1-pentenyl)cyclohexyl]acetophenone in 16 ml of ethanol and 16 ml of diethylene glycol was treated with 0.486 ml of hydrazine hydrate while gassing with argon and then heated to reflux (bath temperature 110° C.) while stirring for 1.5 hours. The mixture was subsequently treated with 550 mg of solid potassium hydroxide, the bath temperature was increased to 210° C. and the ethanol was distilled off. After 2.5 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 (1.23 g) on silica gel with hexane as the eluent gave 1.16 g (91%) of 4-ethyl-1-[trans-4-(trans-1-pentenyl)cyclohexyl]benzene as a colourless oil; m.p. (C-I) -3.1° C.

Workup

  1. temperatureheated
  2. temperaturethe bath temperature was increased to 210° C.
  3. distillationthe ethanol was distilled off
  4. waitAfter 2.5 hours at 210° C.
  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 (1.23 g) on silica gel with hexane as the eluent

Sources & evidence

ORD record
ord-d94e8e8e5088469580117ca055393141
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

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