Hydrochloric Acid → HCID 54435495, compound

HRID 1534680Notes

Reaction equation

HRID 1534680 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:19][C:18]=2[OH:29])=[O:16])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].Cl>CC(C)=O>[CH2:37]([O:36][C:34]([CH2:33][O:29][C:18]1[CH:19]=[C:20]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[CH:14]=[CH:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=1)=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 53635528HCID 53635528, compound

Product 1

HCID 54435495HCID 54435495, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5.50 g of 4-n-hexyl-2'-hydroxy-4'-(3-methyl-2-butenyloxy)chalcone in 55 ml of dry acetone was added 1.4 g of crushed potassium hydroxide. After stirring for 5 minutes, 2.40 g of ethyl bromoacetate was added, and the mixture was stirred at room temperature for 40 minutes. After completion of the reaction, the reaction mixture was neutralized by adding dropwise dilute hydrochloric acid with ice cooling. The precipitated solid was collected by filtration, washed with water, dried and recrystallized from ethanol to give 5.73 g of 2'-ethoxycarbonylmethoxy-4-n-hexyl-4'-(3-methyl-2-butenyloxy)chalcone as pale yellow needles.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 minutes
  2. customAfter completion of the reaction
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0dca6a32c9724213b7a65a61ddfc8813
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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