Acetic Acid → N-(4-Fluorobenzylidene)aniline

HRID 2253867Notes

Reaction equation

HRID 2253867 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 recrystallize 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 recrystallize as needles (28 g, 70%)

Sources & evidence

ORD record
ord-a5a88fdc0f8f4d1dbd847707efe99421
Source dataset
uspto-grants-1993_08
Patent number
US05233046

Reaction notes

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