Water → HCID 178445662, compound

HRID 1709150Notes

Reaction equation

HRID 1709150 reaction equation
[Na].[CH2:2]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14]CC)=[O:13])[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5].O>C(O)C>[CH2:2]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 178445665HCID 178445665, compound

Product 1

HCID 178445662HCID 178445662, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Sodium (7.5 g, 0.33 mol) was dissolved in anhydrous ethanol (200 ml) and ethyl cis-4-n-butylcyclohexanecarboxylate (13) was added. The reaction mixture was heated at reflux for 16 hr and was then cooled to 20° C. Water (38 ml) was added and the mixture was re-heated to reflux for a further 24 hr. The resulting mixture was evaporated to a small volume and the residue was dissolved in water (115 ml). The solution was acidified using concentrated hydrochloric acid and the product was then extracted into dichloromethane (4×50 ml). The combined dichloromethane extracts were evaporated to give predominantly trans-4-n-butylcyclohexanecarboxylic acid (11, 45.6 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hr
  3. temperaturethe mixture was re-heated
  4. temperatureto reflux for a further 24 hr
  5. customThe resulting mixture was evaporated to a small volume
  6. dissolutionthe residue was dissolved in water (115 ml)
  7. extractionthe product was then extracted into dichloromethane (4×50 ml)
  8. customThe combined dichloromethane extracts were evaporated

Sources & evidence

ORD record
ord-b6a1440023a24a9b8d9ee06b423d16a6
Source dataset
uspto-grants-1990_08
Patent number
US04948790

Reaction notes

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