Water → 9-(2,6,6-Trimethylcyclohex-1-en-1-yl)nonanoic acid

HRID 1055184Notes

Reaction equation

HRID 1055184 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19].[OH-].[K+].O>C(O)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 71089603Ethyl 9-(2,6,6-trimethylcyclohex-1-en-1-yl)nonanoate

Product 1

HCID 710896289-(2,6,6-Trimethylcyclohex-1-en-1-yl)nonanoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 9-(2,6,6-trimethylcyclohex-1-en-1-yl)nonanoate (13.2 g, 42.9 mmol) in ethanol (80 mL) was added 4 M KOH (43 mL). The mixture was stirred at room temperature for 1.5 h. Water (350 mL) was added and the solution was washed with tert-butyl methyl ether (2×100 mL). The SimVA, aqueous phase was cooled, acidified with 4 M HCl (˜45 mL) and extracted with pentane (3×100 mL). The combined pentane extracts were washed with water (200 mL), dried (MgSO4), filtered, concentrated and dried under high vacuum. The material was redissolved in pentane (100 mL), concentrated and dried under high vacuum one more time to give 9-(2,6,6-trimethylcyclohex-1-en-1-yl)nonanoic acid as a colorless oil (11.1 g, 92% yield). MS ESI− m/z 279 [M−H]−.

Workup

  1. washthe solution was washed with tert-butyl methyl ether (2×100 mL)
  2. temperatureThe SimVA, aqueous phase was cooled
  3. extractionextracted with pentane (3×100 mL)
  4. washThe combined pentane extracts were washed with water (200 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under high vacuum
  9. dissolutionThe material was redissolved in pentane (100 mL)
  10. concentrationconcentrated
  11. customdried under high vacuum one more time

Sources & evidence

ORD record
ord-5fe86ae9af884f709a9b3c85a2e5e7fa
Source dataset
uspto-grants-2016_07
Patent number
US09393315B2

Reaction notes

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