Diethylene Glycol → HCID 178444309, compound

HRID 1285052Notes

Reaction equation

HRID 1285052 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)[CH2:19][CH3:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].O.NN.C(O)COCCO.[OH-].[K+]>C(O)C>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([C@H:9]2[CH2:8][CH2:7][C@H:6](/[CH:1]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 178444337HCID 178444337, compound

Product 1

HCID 178444309HCID 178444309, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 235 mg of p-[trans-4-(trans-1-pentenyl)cyclohexyl]propiophenone (prepared according to Example 1), 0.161 ml of hydrazine hydrate, 5 ml of diethylene glycol and 5 ml of ethanol was heated to reflux for 30 minutes under an argon atmosphere in a round flask provided with a reflux condenser. The mixture was then treated with 195 mg of solid potassium hydroxide and subsequently gradually heated to 200° C., while distilling off the ethanol, and held at this temperature for 2 hours. The cooled mixture was poured into 50 ml of water and extracted three times with 50 ml of petroleum ether each time. The organic phases were washed three times with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue with hexane on a short column of silica gel gave 185 mg (83%) of 4-propyl-1-[trans-4-(trans-1-pentenyl)cyclohexyl]benzene as a colourless liquid; purity 98.6%, m.p. (C-I) 7.0° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes under an argon atmosphere in a round flask
  3. customprovided with a reflux condenser
  4. distillationwhile distilling off the ethanol
  5. additionThe cooled mixture was poured into 50 ml of water
  6. extractionextracted three times with 50 ml of petroleum ether each time
  7. washThe organic phases were washed three times with 50 ml of water each time
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ae82d0b0226d4260aba9d63992876261
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

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