Ethanol → Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate

HRID 1503634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503634
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].C(O)C>CC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[O:8])[CH:9]=[CH:10][C:11]=1[O:12][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])[CH3:2]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 8467EthylvanillinHCID 11430Potassium Carbonate

Produkt 1

HCID 880082Ethyl 2-(2-ethoxy-4-formylphenoxy)acetateAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The compound was prepared according to general procedure E with 3-ethoxy-4-hydroxybenzaldehyde (2.4 mmol) in dry acetone (15 ml), anhydrous K2CO3 (3.1 mmol), and ethylbromoacetate (3.6 mmol) at reflux for 1 h30. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 565 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 385 mg of purified compound were obtained (63% yield). 1H NMR (250 MHz, CDCl3): δ 1.31 (t, J=7.0 Hz, 3H), 1.49 (t, J=7.0 Hz, 3H), 4.18 (q, J=7.0 Hz, 2H), 4.31 (q, J=7.0 Hz, 2H), 4.79 (s, 2H), 6.91 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.45 (s, 1H) 9.86 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 14.0, 14.5, 61.2, 64.4, 65.9, 111.2, 113.0, 125.5, 131.0, 149.1, 152.7, 168.1, 191.5. MS (ESI): m/z 253.0 [M+H]+.

Aufarbeitung

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h30
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom565 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-58523edf728746dbb1caec96a52ac10c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212196B2

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