Hydrochloric Acid → 5-(4'-Hydroxy-3'methoxyphenyl)pentadienoic acid prenylamide

HRID 654341Notes

Reaction equation

HRID 654341 reaction equation
[CH2:1]([NH:6][C:7](=[O:26])[CH:8]=[CH:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]C(OCC)=O)=[C:14]([O:24][CH3:25])[CH:13]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([NH:6][C:7](=[O:26])[CH:8]=[CH:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:24][CH3:25])[CH:13]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 543244305-(4'-Ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamide

Product 1

HCID 539937655-(4'-Hydroxy-3'methoxyphenyl)pentadienoic acid prenylamideYield 71.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.34 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamide in 10 ml of methanol are added 2.8 ml of 2N aqueous solution of sodium hydroxide followed by stirring at room temperature for 15 min. The mixture is acidified with 1N hydrochloric acid and then extracted with chloroform. The organic layer is washed with water and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with methylene chloride is obtained 0.77 g of 5-(4'-hydroxy-3'methoxyphenyl)pentadienoic acid prenylamide (11). Spectroscopic data of the product support the structure of the formula (11) below.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washFrom the fraction eluted with methylene chloride

Sources & evidence

ORD record
ord-f30aecd1087e4ea2bd8ee842d1ef9a8a
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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