Hydrochloric Acid → HCID 178444556, compound

HRID 653370Notes

Reaction equation

HRID 653370 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-(trans-1-pentenyl)cyclohexanecarboxylic acid and 20 ml of a 11% (wt./vol.) solution of potassium hydroxide in diethylene glycol was boiled at reflux for 20 hours while gassing with argon. The mixture was subsequently made slightly acid with 25% hydrochloric acid and partitioned three times in water/methylene 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 resulting, dark brown, crystallizing oil (1.17 g) from 50 ml of petroleum ether at -78° C. gave 0.44 g of trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid as pale brown crystals. The mother liquor containing 0.695 g of crude cis/trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid was not worked-up.

Workup

  1. temperatureat reflux for 20 hours
  2. custompartitioned three times in water/methylene 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 resulting
  9. customdark brown, crystallizing oil (1.17 g) from 50 ml of petroleum ether at -78° C.

Sources & evidence

ORD record
ord-a91a368e736d42e587dc94006d920c41
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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