Potassium Carbonate → HCID 53657813, compound

HRID 2231448Notes

Reaction equation

HRID 2231448 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([OH:15])[C:7]=1[CH2:16][CH2:17][CH3:18].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][O:15][C:8]1[C:9]([C:12](=[O:14])[CH3:13])=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][Br:1])[C:7]=1[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 60984Methyl bromoacetateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone

Product 1

HCID 53657813HCID 53657813, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g of 1-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone, 3.0 ml of methyl bromoacetate, and 3.3 g of anhydrous potassium carbonate in 75 ml of anhydrous acetone was stirred at reflux for 4 hours. An additional 2.0 g of potassium carbonate was added and reflux was continued for 13 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was purified by high pressure liquid chromatography using 5% ethyl acetate-toluene to give 3.5 g (58%) of [6-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]acetic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturereflux
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo to an oil which
  5. customwas purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-a89005f59d3241d9ac0ec64da2c83028
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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