Reaktion #164843

Reaktionsgleichung

2-Chlorobenzaldehyde

acetone

sodium hydroxide

water

→

yellow solid

Ausbeute 67.5%

1,5-Bis(2-chlorophenyl)-1,4-pentadien-3-one

Ausbeute 67.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 18 hr at room temperature
2. 2
   FiltrationThe resulting precipitate was filtered
3. 3
   Sonstigerecrystallized from ethyl acetate

Vorschrift

2-Chlorobenzaldehyde (1z, 2.00 ml, 17.8 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 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate to give 1.80 g (67%) of a yellow solid: mp 119-121° C. [expected mp 110° C.]; 1H NMR: δ 7.04 (d, 2H, J=16.1 Hz), 7.29 (m, 4H), 7.41 (m, 2H), 7.67 (m, 2H), 8.11 (d, 2H, J=16.1 Hz); 13C NMR: δ 127.0, 127.5, 127.6, 130.1, 131.1, 132.9, 135.3, 139.2, 188.4.

Quelle