Acetic Acid → N-(4-Fluorobenzylidene)aniline

HRID 1492657Notes

Reaction equation

HRID 1492657 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]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 241BenzeneHCID 6115AnilineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 918392N-(4-Fluorobenzylidene)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturethe mixture is heated
  2. customwas azeotropically removed
  3. customThe solvent is evaporated
  4. temperaturethe residual oil upon cooling
  5. customcrystallized
  6. 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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