Potassium Carbonate → Methyl 2-(2-chloro-4-hydroxymethyl-6-methoxyphenoxy)-2-phenylacetate

HRID 1609531

Reaktionsgleichung

Reaktionsgleichung von HRID 1609531
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH2:5][OH:6].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[O:10][CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:14]=1)[C:21]([O:23][CH3:24])=[O:22]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 41816553-Chloro-4-hydroxy-5-methoxybenzyl alcoholHCID 8063364Methyl 2-(2-bromophenyl)acetate

Produkt 1

HCID 19385663Methyl 2-(2-chloro-4-hydroxymethyl-6-methoxyphenoxy)-2-phenylacetateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 0.500 g (2.65 mmol) of 3-chloro-4-hydroxy-5-methoxybenzyl alcohol (Bader) and 0.668 g (1.1 eq) of methyl 2-bromophenylacetate dissolved in 5 mL acetone was added 0.733 g (2 eq) of anhydrous potassium carbonate and the reaction mixture was stirred and refluxed overnight. The reaction mixture was cooled to room temperature, filtered and evaporated in vacuo. The residual oil was purified on a silica gel flash chromatography column eluted with 35% ethyl acetate/hexane to afford 0.570 g (64%) of the title compound.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residual oil was purified on a silica gel flash chromatography column
  5. washeluted with 35% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-939790b1075a4e3fa478c663486fd74d
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05401745

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