Potassium Hydroxide → HCID 53815505, compound

HRID 1979823Notes

Reaction equation

HRID 1979823 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:21])=[CH:15][C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=1>C(O)(C)C>[CH3:3][C:4]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:5][CH:6]=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([CH3:21])=[CH:15][C:16]([OH:18])=[O:17])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54272817HCID 54272817, compound

Product 1

HCID 53815505HCID 53815505, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.4 g of potassium hydroxide was dissolved in 100 ml of isopropanol. 14 g of ethyl 3-[4-(4,8-dimethyl-1,3,7-nonatrienyl)phenyl]-2-butenoate was added to the solution under heating, reflux and stirring. After 30 min, the resulting solution was poured into ice/water and extracted with 100 ml of n-hexane. The aqueous layer was made acidic with dilute hydrochloric acid, extracted with ethyl ether and washed with water. After drying over magnesium sulfate, the product was concentrated and the resulting concentrate was crystallized from n-hexane to obtain 8 g of intended 3-[4-(4,8-dimethyl-1,3,7-nonatrienyl)phenyl]-2-butenoic acid as light yellow crystals.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. extractionextracted with 100 ml of n-hexane
  4. extractionextracted with ethyl ether
  5. washwashed with water
  6. dry with materialAfter drying over magnesium sulfate
  7. concentrationthe product was concentrated
  8. concentrationthe resulting concentrate
  9. customwas crystallized from n-hexane

Sources & evidence

ORD record
ord-03218b4748754906826d2cf4f71bd63a
Source dataset
uspto-grants-1984_11
Patent number
US04482734

Reaction notes

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