Reaktion #417933

Reaktionsgleichung

toluene

phenyl 3-phenylbutanoate

water

→

dark oil

Ausbeute 38.0%

1-(2-hydroxyphenyl)-3-phenylbutan-1-one

Ausbeute 38.0%

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 90° C.
2. 2
   TemperaturThe mixture was cooled to 5° C.
3. 3
   Sonstigethe temperature below 10° C
4. 4
   SonstigeThe mixture was then transferred into a separatory funnel
5. 5
   Sonstigethe phases separated
6. 6
   Waschenthe organic layer washed twice with water
7. 7
   TrocknenThe organic layer was dried with MgSO4
8. 8
   Sonstigethe solvent removed in a rotary evaporator
9. 9
   Sonstigethe residue thoroughly dried

Vorschrift

Titanium(IV) chloride (7.89 g, 41.6 mmol) was dissolved in 1,2-dichloroethane (30 ml). To this solution was added dropwise at room temperature the solution of phenyl 3-phenylbutanoate (10 g, 41.6 mmol) in 1,2-dichloroethane (20 ml). The resulting dark brown solution was heated to 130° C. for 6 h, then cooled to 90° C. and toluene (40 ml) was added. The mixture was cooled to 5° C. and water (40 ml) was added carefully to keep the temperature below 10° C. The mixture was then transferred into a separatory funnel, the phases separated and the organic layer washed twice with water, then twice with 1 N aq. NaOH-solution (100 ml), followed by six washes with half saturated brine. The organic layer was dried with MgSO4 and the solvent removed in a rotary evaporator and the residue thoroughly dried to yield 3.82 g (38%) of a dark oil, which was bulb-to-bulb distilled at 170-180° C./0.05 mbar to yield 1.74 g (17%), which was further purified by column flash chromatography on silica to obtain 1.2 g (12%) of product, which was finally recrystallized from hexane/toluene 2:1 to yield 1.1 g (11%) of product as white crystals, melting point 76.8° C.

Quelle