Ethanol → HCID 178442127, compound

HRID 2231614Notes

Reaction equation

HRID 2231614 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H](C#N)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-:22].[K+].[CH2:24]([OH:26])[CH3:25]>O>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:25]([C:24]([OH:22])=[O:26])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 178442126HCID 178442126, compound

Product 1

HCID 178442127HCID 178442127, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 567 mg of trans-4-[2-(p-pentylphenyl)ethyl]cyclohexanecarbonitrile and 20 ml of a 10:1 mixture of 2N potassium hydroxide and ethanol was heated to reflux for 2 hours while gassing with argon in a round flask fitted with a reflux condenser. The cooled mixture was diluted with 20 ml of water and extracted twice with 30 ml of diethyl ether each time. The separated aqueous phase was acidified with about 20 ml of 2N sulphuric acid and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of saturated sodium chloride solution each time, dried over magnesium sulphate and concentrated. There were obtained 490 mg (81%) of trans-4-[2-(p-pentylphenyl)ethyl]cyclohexanecarboxylic acid as colourless crystals which were purified further by recrystallization from hexane.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customwhile gassing with argon in a round flask
  4. customfitted with a reflux condenser
  5. extractionextracted twice with 30 ml of diethyl ether each time
  6. extractionextracted three times with 50 ml of diethyl ether each time
  7. washThe organic phases were washed twice with 50 ml of saturated sodium chloride solution each time
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-50f0f04e3d2d481f99d58fa4565c51ae
Source dataset
uspto-grants-1988_11
Patent number
US04783280

Reaction notes

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