Hydrogen Peroxide → 2-(2-Hydroxyethyl)benzaldehyde ethylene acetal

HRID 1418365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418365
B.CSC.[CH2:5]1[O:17][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[CH2:16])[O:7][CH2:6]1.[OH-:18].[Na+].OO>C1COCC1.O>[CH2:6]1[O:7][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][OH:18])[O:17][CH2:5]1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 570815972-Vinylbenzaldehyde ethylene acetal

Produkt 1

HCID 552660812-(2-Hydroxyethyl)benzaldehyde ethylene acetal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Borane-dimethyl sulphide complex (2.0M in THF, 7.67 ml, 15.3 mmol) was added dropwise to 2-vinylbenzaldehyde ethylene acetal (2.7 g, 15.3 mmol) in THF (80 ml) at 0° C. Stirring was continued at room temperature for 4 h, cooled to 0° C. and 10% aqueous sodium hydroxide (3 ml) added dropwise, followed by hydrogen peroxide (30% by volume, 1.8 ml). After 1 h at room temperature, the mixture was diluted with water, extracted with ethyl acetate, dried over sodium sulphate and evaporated to give a colourless viscous gum (2.2 g), MS (+EI) 194 (M+), 1H NMR (CDCl3) 7.48 (1H, d, J6 Hz), 7.3-7.1 (3H, m), 5.91 (1H, s), 4.1-3.9 (4H, m), 3.78 (2H, t, J6.5 Hz), 2.93 (2H, t, J6.5 Hz).

Aufarbeitung

  1. waitAfter 1 h at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-63ba1b30111a4f9ebb9150f64dcfb5f3
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883102

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