Diethyl Ether → Ethyl 2-(2-chlorophenoxy)acetate

HRID 18828

Reaktionsgleichung

Reaktionsgleichung von HRID 18828
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 72452-ChlorophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 302826Ethyl 2-(2-chlorophenoxy)acetateAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chlorophenol (2.06 mL, 19.9 mmol) in DMF (40 mL) is added potassium carbonate (3.03 g, 21.9 mmol) and ethyl bromoacetate (2.3 mL, 20.7 mmol), and the mixture is stirred at 80° C. for 18 h. Et2O is added, and the mixture is washed with water, brine, dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is purified by chromatography in silica gel; elution with EtOAc:dichloromethane:hexane (10:5:85) gives 4.17 g of the product 465. 1H NMR (CDCl3) δ 7.38 (d, 1H), 7.21 (t, 1H), 6.92 (t, 1H), 6.84 (d, 1H), 4.70 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H); MS: m/z 215, 217 (M++1).

Aufarbeitung

  1. washthe mixture is washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by chromatography in silica gel
  6. washelution with EtOAc:dichloromethane:hexane (10:5:85)

Quellen und Nachweise

ORD-Eintrag
ord-b29967885a46478f8ec56bcdaffb4281
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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