Réaction #50469

Équation de réaction

NaOH

acetophenone

4-fluorobenzaldehyde

→

pale yellow solid

Rendement 91.9%

3-(4-fluorophenyl)-1-phenyl-2-propen-1-one

Rendement 91.9%

Solvants

H2O

EtOH

Conditions de réaction

Traitement

1. 1
   Autreto 25° C.
2. 2
   Autrereturned to 15° C.
3. 3
   Autrethe cooling bath was removed
4. 4
   Températureto cool overnight at 10° C
5. 5
   FiltrationThis mixture was filtered
6. 6
   Lavagethe solids were washed with distilled H2O until the washings
7. 7
   AutreUpon drying in vacuo

Mode opératoire

To a mechanically stirred solution of 5.0 g NaOH in 35 ml H2O and 25 ml EtOH at 15° C. was added 12.0 g (0.100 mole) of acetophenone and 12.4 g (0.100 mole) of 4-fluorobenzaldehyde. After a brief exotherm to 25° C., the temperature returned to 15° C., and the cooling bath was removed. The reaction mixture was stirred at room temperature for 1.5 hour, and the thick slurry was transferred to a beaker to cool overnight at 10° C. This mixture was filtered, and the solids were washed with distilled H2O until the washings were neutral to litmus. Upon drying in vacuo, 20.8 g of a pale yellow solid was obtained, m.p. 86°-87° C. IR (Nujol): 1660, 1605, 1590, 1580 cm-1. 1H NMR (200 MHz, CDCl3): δ 7.12 (d, J=16 Hz, 1H), 7.42-7.68 (m, 7H), 7.78 (d, J=16 Hz, 1H), 8.02 (m, 2H).

Source