Potassium Hydroxide → 4-(2,6,10-Trimethylundeca-1,5,9-trien-1-yl)benzoic acid

HRID 1979824Notes

Reaction equation

HRID 1979824 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1>C(O)(C)C>[CH3:3][C:4]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54490562HCID 54490562, compound

Product 1

HCID 537995854-(2,6,10-Trimethylundeca-1,5,9-trien-1-yl)benzoic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

20 g of potassium hydroxide was dissolved in 200 ml of isopropanol. 50 g of ethyl p-(2,6,10-trimethyl-1,5,9-undecatrienyl)benzoate was added to the solution under heating, reflux and stirring. After 10 min, the solution was poured into ice/water and extracted with 200 ml of n-hexane. The aqueous layer was made acidic with dilute hydrochloric acid, extracted with ethyl ether, washed with water and dried over magnesium sulfate. The product was concentrated to obtain 42 g of crude crystals. The crude crystals were recrystallized from 150 ml of n-hexane to obtain 32 g of intended p-(2,6,10-trimethyl-1,5,9-undecatrienyl)benzoic acid as white crystals.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. extractionextracted with 200 ml of n-hexane
  4. extractionextracted with ethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe product was concentrated
  8. customto obtain 42 g of crude crystals
  9. customThe crude crystals were recrystallized from 150 ml of n-hexane

Sources & evidence

ORD record
ord-df9353b833a44da6a906886720c90fda
Source dataset
uspto-grants-1984_11
Patent number
US04482734

Reaction notes

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