Reaktion #159766

Reaktionsgleichung

5-bromo-2-methoxybenzaldehyde

ethylene glycol

p-toluenesulfonic acid monohydrate

→

2-(5-bromo-2-methoxy-phenyl)-[1,3]dioxolane

Ausbeute 62.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was azeotroped for 2 h
2. 2
   Sonstigequenched with sat. NaHCO3 (50 mL)
3. 3
   SonstigeReaction mixture
4. 4
   Einengenwas concentrated under reduced pressure
5. 5
   Extraktionextracted with ethyl acetate (2×100 mL)
6. 6
   Waschenwashed with water, brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Einengenconcentrated
9. 9
   Sonstigepurified by silica gel column chromatography

Vorschrift

To a stirred solution of 5-bromo-2-methoxybenzaldehyde (5.0 g, 23.25 mmol) in toluene (50 mL) was added ethylene glycol (2.6 mL, 46.5 mmol) and p-toluenesulfonic acid monohydrate (0.45 g, 2.32 mmol) and the reaction mixture was azeotroped for 2 h, quenched with sat. NaHCO3 (50 mL). Reaction mixture was concentrated under reduced pressure, extracted with ethyl acetate (2×100 mL), washed with water, brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 2-(5-bromo-2-methoxy-phenyl)-[1,3]dioxolane (3.75 g).

Quelle