Reaktion #805721

Reaktionsgleichung

AcOH

benzyltriphenylphosphonium bromide

4-(4-Hydroxyphenyl)butan-2-one

→

title compound

Ausbeute 44.0%

4-(3-Methyl-4-phenylbut-3-enyl)phenol

Ausbeute 44.0%

Lösungsmittel

—

hexanes

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL)
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe residue was purified by flash chromatography on SiO2

Vorschrift

To a suspension of benzyltriphenylphosphonium bromide (10.9 g, 25.1 mmol, 1.2 equiv.) in THF (35 mL), was added potassium-t-amylat (1.7 M in toluene, 20 mL, 34.0 mmol, 1.7 equiv.) at 25° C. 4-(4-Hydroxyphenyl)butan-2-one (3.3 g, 20.1 mmol, 1.0 equiv.) in THF (5 mL) was added to the red suspension, and the mixture was stirred at 70° C. for 30 min. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was diluted with hexanes (50 mL). The organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL) and concentrated. The residue was purified by flash chromatography on SiO2 to yield 2.10 g (44%) of the title compound as a white solid.

Quelle