2,5-Dimethylphenol → 4-(2,5-Dimethylphenoxy)butanoic acid

HRID 341345

Reaktionsgleichung

Reaktionsgleichung von HRID 341345
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[O-]CC.[Na+].Br[CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19].[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Komponenten

7

Edukt 4

HCID 72672,5-DimethylphenolHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 2723922Sodium ethoxide

Produkt 1

HCID 15684184-(2,5-Dimethylphenoxy)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

2,5-dimethylphenol (24.5 g, 0.2 mol) was dissolved in 125 ml of anhydrous ethanol. To the solution was added 75 ml of 21 wt % sodium ethoxide solution in ethanol (0.2 mol). The mixture solution was stirred at room temperature for 10 min. Ethyl 4-bromobutyrate (40 g, 0.205 mol) was then added to the solution. The reaction mixture was refluxed at 80° C. for 24 h. The precipitate was filtered off. The filtrate was then mixed with a solution of sodium hydroxide (10 g, 0.25 mol) in 150 ml of water. The mixture was stirred at 70° C. for about 2 hours, monitored with HPLC. It was diluted with 150 ml of water and acidified to pH 1. Oily precipitate formed immediately. It was collected by decanting the supernatant and washed with water twice (100 ml×2). The oily precipitate solidified after kept in water at room temperature overnight.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed at 80° C. for 24 h
  2. filtrationThe precipitate was filtered off
  3. stirringThe mixture was stirred at 70° C. for about 2 hours
  4. customOily precipitate formed immediately
  5. customIt was collected
  6. customby decanting the supernatant
  7. washwashed with water twice (100 ml×2)
  8. waitafter kept in water at room temperature overnight

Quellen und Nachweise

ORD-Eintrag
ord-74130aaf3cf647d99a96805bcd530674
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895777B2

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