Water → n-Butyl 2-(p-prenylphenyl)propionate

HRID 904922Notes

Reaction equation

HRID 904922 reaction equation
[OH-].[K+].[CH2:3](Br)[CH2:4][CH2:5][CH3:6].O.[CH2:9]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1)[CH:10]=[C:11]([CH3:13])[CH3:12]>CN(C)P(=O)(N(C)C)N(C)C.C(O)C>[CH2:9]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:24])[C:21]([O:23][CH2:3][CH2:4][CH2:5][CH3:6])=[O:22])=[CH:18][CH:19]=1)[CH:10]=[C:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

Product 1

HCID 13118084n-Butyl 2-(p-prenylphenyl)propionateYield 63.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

Six grams of powdered potassium hydroxide was dissolved in a mixture of 21.8 g of 2-(p-prenylphenyl)propionic acid in 125 ml of hexamethylphosphoric triamide and 125 ml of ethyl alcohol with stirring at room temperature. To the solution was added 27.4 g of n-butyl bromide and the mixture was stirred at room temperature for 24 hours. The mixture was poured into 500 ml of water and extracted with n-hexane. The extract was washed with 2 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 17.3 g of n-butyl 2-(p-prenylphenyl)propionate. b.p. 131°-133° C./0.15 mmHg, IR νmaxneat ; 1730 cm-1.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. extractionextracted with n-hexane
  3. washThe extract was washed with 2 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-78547cedc89f4a02890a9b50fe68dc2a
Source dataset
uspto-grants-1983_12
Patent number
US04420631

Reaction notes

Loading…