Potassium Carbonate → HCID 53945181, compound

HRID 2164921Notes

Reaction equation

HRID 2164921 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][O:16][C:17](=[O:37])[CH2:18][O:19][C:20]1[C:25]([C:26](=[O:28])[CH3:27])=[CH:24][CH:23]=[C:22]([O:29][CH2:30][CH2:31][CH2:32]Br)[C:21]=1[CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:15][O:16][C:17](=[O:37])[CH2:18][O:19][C:20]1[C:25]([C:26](=[O:28])[CH3:27])=[CH:24][CH:23]=[C:22]([O:29][CH2:30][CH2:31][CH2:32][O:11][C:6]2[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=2[CH2:8][CH2:9][CH3:10])[C:21]=1[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 53657813HCID 53657813, compound

Product 1

HCID 53945181HCID 53945181, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.72 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 3.43 g of [6-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]acetic acid methyl ester, 2.44 g of anhydrous potassium carbonate in 50 ml of anhydrous acetone and 25 ml of anhydrous dimethylformamide was stirred at reflux for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified by high pressure liquid chromatography to give 1.45 g (33%) of [6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-fefa3762792f418698fd34271cc1f421
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

Loading…