Potassium Carbonate → HCID 53657813, compound

HRID 2164920Notes

Reaction equation

HRID 2164920 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-9dbeb8e378cd4b159994c6de6bdf6fc7
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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