Acetophenone → 3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one

HRID 326288Notes

Reaction equation

HRID 326288 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1>O.CCO>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 982013-(4-Fluorophenyl)-1-phenylprop-2-en-1-oneYield 91.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. customto 25° C.
  2. customreturned to 15° C.
  3. customthe cooling bath was removed
  4. temperatureto cool overnight at 10° C
  5. filtrationThis mixture was filtered
  6. washthe solids were washed with distilled H2O until the washings
  7. customUpon drying in vacuo

Sources & evidence

ORD record
ord-c06037edd72145d7be35ac42d5fe8990
Source dataset
uspto-grants-1993_12
Patent number
US05268388

Reaction notes

Loading…