Hydrochloric Acid → HCID 178444514, compound

HRID 2050437Notes

Reaction equation

HRID 2050437 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H](C#N)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[OH-:20].[K+].Cl.C(O)CO[CH2:26][CH2:27][OH:28]>>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:26]([C:27]([OH:28])=[O:20])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 178444506HCID 178444506, compound

Product 1

HCID 178444514HCID 178444514, compound

Conditions

Temperature
130 °C

Procedure

A solution of 1.71 g of trans-4-[trans-4-(4-pentenyl)cyclohexyl]cyclohexanecarbonitrile (prepared according to Example 2) in 30 ml of diethylene glycol was treated with 3.11 g of potassium hydroxide and stirred at 130° C. for 3 hours. The mixture was then poured on to ice-water, acidified with 25 percent hydrochloric acid and extracted three times with diethyl ether. The organic phases were combined, washed three times with water, dried over magnesium sulfate and evaporated. Recrystallization of the brown, crystalline residue (1.74 g) from 30 ml of hexane gave 996 mg of trans-4-[trans-4-(4-pentenyl)cyclohexyl]cyclohexanecarboxylic acid as yellowish crystals.

Workup

  1. extractionextracted three times with diethyl ether
  2. washwashed three times with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customRecrystallization of the brown, crystalline residue (1.74 g) from 30 ml of hexane

Sources & evidence

ORD record
ord-4e17b0c924ac4d6397ca1096bd73b790
Source dataset
uspto-grants-1991_05
Patent number
US05013477

Reaction notes

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