Potassium Hydroxide → 2-Cyclohexylideneacetic acid

HRID 1244452

Reaction equation

HRID 1244452 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:14])[CH:7]=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)C>O.CO>[C:8]1(=[CH:7][C:6]([OH:14])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 73776Ethyl cyclohexylideneacetate

Product 1

HCID 962062-Cyclohexylideneacetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of KOH (1.0 g, 18 mmol) dissolved in water (25 mL) and Intermediate 3 (1.6 g, 9.5 mmol) dissolved in MeOH (5 mL) was stirred for 18 hours at room temperature. The reaction was refluxed for one hour, cooled, then extracted with EtOAc. The aqueous layer was acidified with 1N NCl and extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated in vacuo to provide 1.3 g (100%) of Intermediate 4. 1H NMR (DMSO-d6) δ: 1.55 (br s, 6H) 2.1 (m, 2H), 2.8 (m, 2H), 5.5 (s, 1H), 11.9 (s, 1H); MS ES−m/e 139.1 (p−1).

Workup

  1. temperatureThe reaction was refluxed for one hour
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-965e90e91c0f4179825256b49f9ee004
Source dataset
uspto-grants-2006_10
Patent number
US07122554B2

Linked notes

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