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

HRID 1388804Notes

Reaction equation

HRID 1388804 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:18])[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].[OH-].[Na+].O>C(O)C>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:18])[C:13]([OH:15])=[O:14])=[CH:10][CH:11]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13118083Ethyl alpha-[p-(3-methyl-2-butenyl)phenyl]propionate

Product 1

HCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acidYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.6 g of ethyl α-(p-prenylphenyl)propionate was dissolved in 250 ml of ethanol, and a solution composed of 6.0 g of sodium hydroxide and 10 ml of water was added. The mixture was stirred overnight at room temperature, and concentrated. Water was added, and the mixtue was washed with diethyl ether. The resulting aqueous layer was acidified with 1 N hydrochloric acid, and extracted with diethyl ether. The extract was washed with an aqueous solution of sodium chloride, dried, concentrated and distilled to give 19.5 g of α-(p-prenylphenyl)propionic acid having the following boiling point and NMR spectrum.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additionWater was added
  4. washthe mixtue was washed with diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with an aqueous solution of sodium chloride
  7. customdried
  8. concentrationconcentrated
  9. distillationdistilled

Sources & evidence

ORD record
ord-e04a8e9b2ecb40a7810471d3332fec59
Source dataset
uspto-grants-1984_02
Patent number
US04433160

Reaction notes

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