Hydrochloric Acid → HCID 67826943, compound

HRID 654345Notes

Reaction equation

HRID 654345 reaction equation
[CH2:1]([NH:11][C:12](=[O:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C(OCC)=O)=[C:17]([O:27][CH3:28])[CH:16]=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:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:27][CH3:28])[CH:16]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67827385HCID 67827385, compound

Product 1

HCID 67826943HCID 67826943, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.44 g of 4-ethoxycarbonyloxy-3-methoxycinnamic 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 anhydrous 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 chloroform is obtained 0.70 g of 4-hydroxy-3-methoxycinnamic acid geranylamide (14). Spectroscopic data of the product support the structure of the formula (14) below.

Workup

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

Sources & evidence

ORD record
ord-6688a609f0554af191a1f7b186dc3138
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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