Vanillin → 2-(4-Formyl-2-methoxyphenoxy)ethyl acetate

HRID 38714

Reaktionsgleichung

Reaktionsgleichung von HRID 38714
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[K+].[K+].[C:18]([O:21][CH2:22][CH2:23]Br)(=[O:20])[CH3:19]>CC(C)=O.C(OCC)C>[C:18]([O:21][CH2:22][CH2:23][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

Produkt 1

HCID 21704232-(4-Formyl-2-methoxyphenoxy)ethyl acetateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-3-methoxy-benzaldehyde (2.5 g, 16.4 mmol), K2CO3 (6.81 g, 49.3 mmol) and 2-bromoethyl acetate (5.49 g, 32.9 mmol) in acetone (50 mL) is refluxed for 48 h before it is diluted with diethyl ether (250 mL) and washed with water (2×200 mL). The washings are extracted with diethyl ether (200 mL). The combined organic extracts are dried over MgSO4 and concentrated. The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1 to afford the title compound (2.94 g) as colourless solid. 1H NMR (CDCl3):δ 9.85 (s, 1H), 7.45-7.41 (m, 2H), 6.99 (d, J=7.6 Hz, 1H), 4.51-4.47 (m, 2H), 4.34-4.30 (m, 2H), 3.94 (s, 3H), 2.11 (s, 3H).

Aufarbeitung

  1. temperatureis refluxed for 48 h before it
  2. washwashed with water (2×200 mL)
  3. extractionThe washings are extracted with diethyl ether (200 mL)
  4. dry with materialThe combined organic extracts are dried over MgSO4
  5. concentrationconcentrated
  6. customThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Quellen und Nachweise

ORD-Eintrag
ord-cf880a8e516a4ef48b42eb713ddc202f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524752B2

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