Hydrochloric Acid → HCID 178443903, compound

HRID 622276Notes

Reaction equation

HRID 622276 reaction equation
[CH2:1]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:20]=[CH:19]C(C#N)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[OH-:21].[K+].Cl.C(O)CO[CH2:27][CH2:28][OH:29]>>[CH2:1]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:20]=[CH:19][C:27]([C:28]([OH:29])=[O:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178443899HCID 178443899, compound

Product 1

HCID 178443903HCID 178443903, compoundYield 104%

Procedure

A mixture of 2.61 g of p-[trans-4-(5-hexenyl)cyclohexyl]benzonitrile and 20 g of potassium hydroxide in 200 ml of diethylene glycol was boiled at 180° C. for 1 hour while gassing with argon in a round flask equipped with a magnetic stirrer and a reflux condenser. After cooling the brown reaction mixture was made acid with 35 ml of 36 percent hydrochloric acid and partitioned between 100 ml of methylene chloride and 100 ml of water. The aqueous phase was back-extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time and dried over magnesium sulphate and active charcoal. After separating the solvent in a rotary evaporator there were obtained 2.93 g (104%) of p-[trans-4-(5-hexenyl)cyclohexyl]benzoic acid as brownish, not quite pure crystals; Rf value 0.38 (ethyl acetate/petroleum ether vol. 3:7).

Workup

  1. customfor 1 hour
  2. customwhile gassing with argon in a round flask
  3. customequipped with a magnetic stirrer and a reflux condenser
  4. temperatureAfter cooling the brown reaction mixture
  5. custompartitioned between 100 ml of methylene chloride and 100 ml of water
  6. extractionThe aqueous phase was back-extracted three times with 100 ml of methylene chloride each time
  7. washThe organic phases were washed twice with 100 ml of water each time
  8. dry with materialdried over magnesium sulphate and active charcoal
  9. customAfter separating the solvent
  10. customin a rotary evaporator there

Sources & evidence

ORD record
ord-7133fc5bb3964ff5b916420fea088237
Source dataset
uspto-grants-1988_09
Patent number
US04770503

Reaction notes

Loading…