Hydrochloric Acid → 4-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester

HRID 1158468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158468
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.C([Li])CCC.CCCCCC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].Cl>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1)[CH3:32]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 10928Ethyl chloroformateHCID 615316034-Bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzeneHCID 178418339Butyllithium

Produkt 1

HCID 686167104-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzene (2.88 g, 10.5 mmol) in absolute THF (30 mL) is added at −70° C. a 1.6N solution of n-butyllithium in hexane (7.20 mL, 11.5 mmol) with stirring. After 40 min, ethyl chloroformate (1.14 g, 10.5 mmol) is added, and the mixture is stirred overnight while gradually warming up to room temperature. The mixture is poured into 2N aqueous HCl, extracted with CH2Cl2, the organic layers are dried (Na2SO4) and concentrated. The crude product is purified by flash chromatography on silica gel (hexane/AcOEt 2:1) to give the title compound as liquid. TLC, Rf (hexane/AcOEt 1:1)=0.13.

Aufarbeitung

  1. stirringthe mixture is stirred overnight
  2. extractionextracted with CH2Cl2
  3. dry with materialthe organic layers are dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography on silica gel (hexane/AcOEt 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3670d441196e4f7d9514326461e07a9d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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