Water → 2-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

HRID 1413833Notes

Reaction equation

HRID 1413833 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:15])[C:13]#N)=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].[OH-:16].[Na+].[OH2:18]>CO>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:15])[C:13]([OH:18])=[O:16])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 135850232-(p-Prenylphenyl)propionitrile

Product 1

HCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 16.4 g of 2-(p-prenylphenyl)propionitrile, 60 g of sodium hydroxide, 100 ml of water and 120 ml of methanol was stirred at 70°-75° C. for 8 hours. The resulting solution was concentrated and acidified with dilute hydrochloric acid, followed by extraction with ethyl ether and washing with water. The ethereal solution was extracted with 5% aqueous potassium hydroxide solution. The aqueous layer was acidified with dilute hydrochloric acid, and extracted with ether, which was then washed with water, dried over anhydrous magnesium sulfate and decolorized with activated charcoal. The ether was removed to give 15.5 g of 2-(p-prenylphenyl)propionic acid. ##STR1##

Workup

  1. concentrationThe resulting solution was concentrated
  2. extractionfollowed by extraction with ethyl ether
  3. washwashing with water
  4. extractionThe ethereal solution was extracted with 5% aqueous potassium hydroxide solution
  5. extractionextracted with ether, which
  6. washwas then washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe ether was removed

Sources & evidence

ORD record
ord-6ec6a089c769436f80a00e4fd1cac617
Source dataset
uspto-grants-1981_02
Patent number
US04251543

Reaction notes

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