Hydrochloric Acid → HCID 178444556, compound

HRID 2254959Notes

Reaction equation

HRID 2254959 reaction equation
[CH:1](/[CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[OH-].[K+].Cl>C(O)COCCO>[CH:1](/[C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19380505HCID 19380505, compound

Product 1

HCID 178444556HCID 178444556, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A mixture of 1.29 g of 4-(1E-pentenyl)cyclohexanecarboxylic acid and 20 ml of a 11 percent (wt./vol.) solution of potassium hydroxide in diethylene glycol was boiled at reflux for 20 hours while gassing with argon. The reaction mixture was subsequently made slightly acid with 25 percent hydrochloric acid and partitioned three times in water/ethylene chloride. The organic extracts were washed twice with water and the wash-water was back-extracted with methylene chloride. The organic phases were dried over magnesium sulphate and freed from solvent on a rotary evaporator. Recrystallization of the dark brown, crystallizing oil obtained (1.17 g) from 50 ml of petroleum ether at -78° C. gave 0.44 g of trans-4-(1E-pentenyl)cyclohexanecarboxylic acid as pale brown crystals. The mother liquor containing 0.695 g of crude cis/trans-4-(1-E-pentenyl)-cyclohexanecarboxylic acid was not worked-up.

Workup

  1. temperatureat reflux for 20 hours
  2. custompartitioned three times in water/ethylene chloride
  3. washThe organic extracts were washed twice with water
  4. washthe wash-water
  5. extractionwas back-extracted with methylene chloride
  6. dry with materialThe organic phases were dried over magnesium sulphate
  7. customfreed from solvent on a rotary evaporator
  8. customRecrystallization of the dark brown,
  9. customcrystallizing oil
  10. customobtained (1.17 g) from 50 ml of petroleum ether at -78° C.

Sources & evidence

ORD record
ord-29f3aab32886487ab50ef98cce27c9c8
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

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