Ethyl bromoacetate → HCID 54393850, compound

HRID 1534687Notes

Reaction equation

HRID 1534687 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:17][C:16]=2[OH:27])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:17][C:16]=2[O:27][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 54478415HCID 54478415, compound

Product 1

HCID 54393850HCID 54393850, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 45.1 g of 4-t-butyl-2'-hydroxy-4'-(3-methyl-2-butenyloxy)chalcone in 500 ml of acetone was added 10.6 g of potassium hydroxide, and the mixture was stirred for 5 minutes. Then, 21.5 g of ethyl bromoacetate was added, and the mixture was stirred for 45 minutes. After neutralization with dilute hydrochloric acid, the precipitated solid was collected by filtration, washed with water, dried and recrystallized from ethanol to give 47.6 g of 4-t-butyl-2'-ethoxycarbonylmethoxy-4'-(3-methyl-2-butenyloxy)chalcone as a pale yellow powder.

Workup

  1. stirringthe mixture was stirred for 45 minutes
  2. filtrationAfter neutralization with dilute hydrochloric acid, the precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d8dcb2bd37924084840dd276647b9863
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

Loading…