Reaktion #164842

Reaktionsgleichung

3-Chlorobenzaldehyde

acetone

sodium hydroxide

water

→

yellow solid

Ausbeute 90.3%

1,5-Bis(3-chlorophenyl)-1,4-pentadien-3-one

Ausbeute 90.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 2 hr at room temperature
2. 2
   FiltrationThe resulting precipitate was filtered
3. 3
   Sonstigerecrystallized from ethyl acetate

Vorschrift

3-Chlorobenzaldehyde (1y, 2.00 ml, 17.7 mmol) and acetone (19, 0.65 ml, 8.8 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (20 ml) was added and the mixture stirred for 2 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 2.41 g (90%) of a yellow solid: mp 125-127° C. [expected mp 120-121° C.]; 1H NMR: δ 7.03 (d, 2H, J=15.9 Hz), 7.33 (m, 4H), 7.45 (d, 2H, J=6.6 Hz), 7.58 (m, 2H), 7.64 (d, 2H, J=15.9 Hz); 13C NMR: δ 126.3, 126.6, 127.9, 130.1, 130.3, 134.9, 136.5, 141.8, 188.0.

Quelle