Hydrochloric Acid → HCID 178444340, compound

HRID 1111493Notes

Reaction equation

HRID 1111493 reaction equation
[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18]C(C#N)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[OH-:20].[K+].Cl.C(O)CO[CH2:26][CH2:27][OH:28]>>[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18][C:26]([C:27]([OH:28])=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444327HCID 178444327, compound

Product 1

HCID 178444340HCID 178444340, compoundYield 92%

Procedure

A mixture of 100 mg of p-[trans-4-(trans-1-pentenyl)-cyclohexyl]benzonitrile and 10 ml of a 10% solution of potassium hydroxide in diethylene glycol was boiled at 180° C. for 1 hour while gassing with argon in a round flask provided with a magnetic stirrer and a reflux condenser. After cooling the brown reaction mixture was made acid with 25% hydrochloric acid and partitioned between 70 ml of dichloromethane and 70 ml of water The aqueous phase was back-extracted three times with 70 ml of dichloromethane each time. The organic phases were washed twice with 70 ml of water each time and dried over magnesium sulphate and active carbon. After separating the solvent in a rotary evaporator there were obtained 99 mg (92%) of p-[trans-4-(trans-1-pentenyl)cyclohexyl]benzoic acid as white, intensively smelling crystals; Rf-value 0.44 (ethyl acetate/petroleum ether, vol. 3:7).

Workup

  1. customfor 1 hour
  2. customwhile gassing with argon in a round flask
  3. customprovided with a magnetic stirrer and a reflux condenser
  4. temperatureAfter cooling the brown reaction mixture
  5. custompartitioned between 70 ml of dichloromethane and 70 ml of water The aqueous phase
  6. extractionwas back-extracted three times with 70 ml of dichloromethane each time
  7. washThe organic phases were washed twice with 70 ml of water each time
  8. dry with materialdried over magnesium sulphate and active carbon
  9. customAfter separating the solvent
  10. customin a rotary evaporator there

Sources & evidence

ORD record
ord-185f8635b31d40759452f2f07be4135f
Source dataset
uspto-grants-1990_12
Patent number
US04980486

Reaction notes

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