Ethyl bromoacetate → Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

HRID 1909571

Reaktionsgleichung

Reaktionsgleichung von HRID 1909571
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:3]([CH3:11])[CH:4]=1)(=[O:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 701354'-Hydroxy-3'-methylacetophenone

Produkt 1

HCID 21986544Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-hydroxy-3-methylphenyl)ethanone (5 g, 33.3 mmol), ethyl 2-bromoacetate (1.1 eq.), and cesium carbonate (2 eq.) in acetonitrile (200 mL) was stirred at room temperature overnight. The acetonitrile was removed in vacuo, and the crude oil was dissolved in ethyl acetate (50 mL) and washed with 1M HCl (2×50 mL), water (2×50 mL), and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to obtain ethyl 2-(4-acetyl-2-methylphenoxy)acetate (683).

Aufarbeitung

  1. customThe acetonitrile was removed in vacuo
  2. dissolutionthe crude oil was dissolved in ethyl acetate (50 mL)
  3. washwashed with 1M HCl (2×50 mL), water (2×50 mL), and brine (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-643e1ec6f4d74f45bb7fafa11fbbb248
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598374B2

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