Ethyl Acetate → Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate

HRID 253239

Reaktionsgleichung

Reaktionsgleichung von HRID 253239
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][O:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:27][CH2:28]C)(=O)[CH3:25]>CN(C=O)C>[CH3:13][O:14][CH2:15][CH2:16][O:1][C:2]1[C:11]([O:12][CH2:25][CH2:24][O:27][CH3:28])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-DihydroxybenzoateHCID 809722-Bromoethyl methyl ether

Produkt 1

HCID 66888836Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of methyl 2,3-dihydroxybenzoate (2.18 g, 12.97 mmol), 2-bromoethyl methyl ether (4.50 g, 32.42 mmol), and potassium carbonate (6.91 g, 50.0 mmol) in DMF (20 mL) was stirred at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate (300 mL), washed with 5% aqueous LiCl (2×50 mL), and brine (50 mL), dried with sodium sulfate, and concentrated to provide crude methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (3.49 g, 95% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ7.32 (dd, 1H), 7.05 (m, 2H), 4.22 (m, 2H), 4.15 (m, 2H), 3.88 (s, 3H), 3.75 (m, 4H), 3.43 (s, 6H).

Aufarbeitung

  1. washwashed with 5% aqueous LiCl (2×50 mL), and brine (50 mL)
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-15bf665e3cb3497ea8c928521ee0839c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872014B2

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