Acetic Acid → N-(4-Fluorobenzylidene)aniline
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC=CC=1.C(O)(=O)C>O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To 4-fluorobenzaldehyde (24.8 g, 0.200 mol) and aniline (18.6 g, 0.200 mol) was added benzene (200 mL) and acetic acid (0.7 mL) and the mixture is heated under reflux until all the water (3.6 mL) was azeotropically removed. The solvent is evaporated and the residual oil upon cooling and stirring crystallized. The white mass was then recrystallized as needles (28 g, 70%): mp 39°-40° C. (PE) (lit.1 mp 40° C.).
Workup
- temperaturethe mixture is heated
- customwas azeotropically removed
- customThe solvent is evaporated
- temperaturethe residual oil upon cooling
- customcrystallized
- customThe white mass was then recrystallized as needles (28 g, 70%)
Sources & evidence
- ORD record
- ord-fa25214b4cea40cab83e37faa36aecfd
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374701
Reaction notes
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