Potassium Iodide → [4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester

HRID 2231443Notes

Reaction equation

HRID 2231443 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].[CH2:15]([O:17][C:18](=[O:38])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([O:30][CH2:31][CH2:32][CH2:33]Br)[C:22]=1[CH2:35][CH2:36][CH3:37])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CN(C)C=O>[CH2:15]([O:17][C:18](=[O:38])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([O:30][CH2:31][CH2:32][CH2:33][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:22]=1[CH2:35][CH2:36][CH3:37])[CH3:16]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 133891464-Acetyl-3-(3-bromopropoxy)-2-propylphenoxy acetic acid ethyl ester

Product 1

HCID 13389148[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid ethyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.17 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 2.41 g of 4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy acetic acid ethyl ester, 1.66 g of anhydrous potassium carbonate and 0.1 g of potassium iodide in 15 ml of anhydrous acetone and 15 ml of anhydrous dimethylformamide was stirred at reflux for 18 hours. The solvent was removed in vacuo, 50 ml of 0.1N hydrochloric acid was added to the residue and the product was extracted with methylene chloride. The dried, over sodium sulfate, extract was concentrated in vacuo and the crude product was crystallized from methanol to yield 2.1 g, mp 45°-46°, (68% yield) of [4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed in vacuo, 50 ml of 0.1N hydrochloric acid
  3. additionwas added to the residue
  4. extractionthe product was extracted with methylene chloride
  5. extractionThe dried, over sodium sulfate, extract
  6. concentrationwas concentrated in vacuo
  7. customthe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-3a3d9d363e2f4390b0a9fe057c52c046
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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