Hydrochloric Acid → HCID 178445640, compound

HRID 1029342Notes

Reaction equation

HRID 1029342 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C@H:11]2[CH2:16][CH2:15][C@H](C#N)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].[OH-:19].[K+].Cl.C(O)CO[CH2:25][CH2:26][OH:27]>>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C@H:11]2[CH2:16][CH2:15][C@H:25]([C:26]([OH:27])=[O:19])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene Glycol2×HCID 14797Potassium HydroxideHCID 178445637HCID 178445637, compound

Product 1

HCID 178445640HCID 178445640, compound

Conditions

Temperature
180 °C

Procedure

A solution of 1.04 g of trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexanecarbonitrile in 10 ml of diethylene glycol was treated with a solution of 2 g of potassium hydroxide in 10 ml of diethylene glycol and then stirred at 180° C. (oil bath temperature) for 2.5 hours. Subsequently, the reaction mixture was poured on to ice/water, acidified with 8 ml of 25 percent hydrochloric acid and extracted with diethyl ether. The organic phase was dried over magnesium sulphate, filtered and evaporated. Crystallization of the resulting beige crude product (1.06 g) from 50 ml of hexane gave 588 mg of trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexanecarboxylic acid as colorless crystals.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customCrystallization of the resulting beige crude product (1.06 g) from 50 ml of hexane

Sources & evidence

ORD record
ord-a441f03b21b643a6b2f042c5b0aaab50
Source dataset
uspto-grants-1992_04
Patent number
US05102578

Reaction notes

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