Potassium Hydroxide → (2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoic acid

HRID 1611063Notes

Reaction equation

HRID 1611063 reaction equation
[OH-].[K+].[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5]\[C:6]([O:8]CC)=[O:7]>CC(O)C>[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5]\[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6370567ethyl(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate

Product 1

HCID 12195841(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoic acidYield 18.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Potassium hydroxide (3.0 g) was dissolved in 30 ml of 2-propanol at 100° C. The solution was added with 2-propanol solution (10 ml) of ethyl (2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate obtained in Example 3 (9.1 g, 34.5 mmol), and stirred at the same temperature for 15 minutes. The reaction mixture was added to ice-water and washed with n-hexane. The solution was neutralized with 10% hydrochloric acid and extracted with n-hexane. The resulting organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from methanol twice to obtain 1.5 g of the title compound (yield 18%) as a yellow crystal.

Workup

  1. washwashed with n-hexane
  2. extractionextracted with n-hexane
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from methanol twice

Sources & evidence

ORD record
ord-90639ba9cd744325b80804610b48a52e
Source dataset
uspto-grants-2006_01
Patent number
US06984742B2

Reaction notes

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