HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 654343
Notes
Print preview

Reaction equation

HRID 654343 reaction equation
[CH2:1]([NH:11][C:12](=[O:31])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C(OCC)=O)=[C:19]([O:29][CH3:30])[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([NH:11][C:12](=[O:31])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:29][CH3:30])[CH:18]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867459905-(4'-Ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide

Product 1

HCID 867459895-(4'-Hydroxy-3-methoxyphenyl)pentadienoic acid geranylamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.61 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid geranylamide in 25 ml of methanol is added 10 ml of 2N aqueous solution of sodium hydroxide. The mixture is stirred at room temperature for one hour. The reaction mixture, after acidified with 1N hydrochloric acid, is extracted with chloroform. The organic layer is washed with water and dried over sodium sulfate. The solvent is 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 1.20 g of 5-(4'-hydroxy-3-methoxyphenyl)pentadienoic acid geranylamide (12). Spectroscopic data of the product support the structure of the formula (12) below.

Workup

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

Sources & evidence

ORD record
ord-dd713cb3697142098f80890c2dcd4e68
Source dataset
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05130483

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes