Potassium Hydroxide → 3,7,11,15-Tetramethylhexadeca-2,4,6,10,14-pentaenoic acid

HRID 841110Notes

Reaction equation

HRID 841110 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:26])[CH:7]=[C:8]([CH3:25])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])C>CC(O)C>[CH3:25][C:8]([CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:7][C:6]([OH:26])=[O:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54362700HCID 54362700, compound

Product 1

HCID 1147413,7,11,15-Tetramethylhexadeca-2,4,6,10,14-pentaenoic acidYield 80.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Under argon atmosphere, potassium hydroxide (19.4 g) was dissolved in 2-propanol (200 ml) under reflux, and the solution was added dropwise with (2E, 4E, 6E, 10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid ethyl ester (48.6 g) dissolved in 2-propanol (50 ml). After the mixture was stirred for 10 minutes under reflux, ice water was added to the reaction mixture and the aqueous layer was washed with n-hexane. The aqueous layer was made acid with 10% aqueous hydrochloric acid, and then extracted with diisopropyl ether. The organic layer was washed with brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain crude (2E, 4E, 6E, 10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (35.7 g, purity: 62.2%) as orange crystals.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. washthe aqueous layer was washed with n-hexane
  4. extractionextracted with diisopropyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-30b7985ae25f44eab19e28231a0ad3f4
Source dataset
uspto-grants-2002_04
Patent number
US06369251B1

Reaction notes

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