Hydrochloric Acid → HCID 178444555, compound

HRID 2254984Notes

Reaction equation

HRID 2254984 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H](C#N)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[OH-:14].[K+].Cl.C(O)CO[CH2:20][CH2:21][OH:22]>>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:20]([C:21]([OH:22])=[O:14])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444522HCID 178444522, compound

Product 1

HCID 178444555HCID 178444555, compoundYield 90%

Conditions

Temperature
180 °C

Procedure

A solution of 2.9 g of trans-4-(4-pentenyl)cyclohexanecarbonitrile in 80 ml of diethylene glycol was treated with 8.0 g of potassium hydroxide and the mixture was stirred for 3.5 hours at a bath temperature of 180° C. Subsequently, the reaction mixture was treated with ice, made acid with 25 ml of 25 percent hydrochloric acid and partitioned in methylene chloride/water. The aqueous phase was extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. Chromatographic separation of the brown, oily residue (3.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 2.9 g (90%) of trans-4-(4-pentenyl)cyclohexanecarboxylic acid as a yellowish oil.

Workup

  1. additionSubsequently, the reaction mixture was treated with ice
  2. custompartitioned in methylene chloride/water
  3. extractionThe aqueous phase was extracted three times with methylene chloride
  4. washThe organic phases were washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatographic separation of the brown, oily residue (3.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90)

Sources & evidence

ORD record
ord-f4d40b076efd488dabe3182071a25828
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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