Ethanol → Salicylideneaniline

HRID 333526Notes

Reaction equation

HRID 333526 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)C>Cl.O>[CH:1](=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

6

Reactant 3

HCID 702EthanolHCID 6115AnilineHCID 6998Salicylaldehyde

Product 1

HCID 136621SalicylideneanilineYield 42.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

To a mixture of salicylaldehyde (40 mL, 45.84 g, 375.37 mmol)) and aniline (22 mL, 31.72 g, 374.66 mmol), was added ethanol (90 mL), 8 drops of concentrated hydrochloric acid and water (10 mL). This reaction mixture was refluxed for one hour, allowed to cool to room temperature and left in the refrigerator over the weekend. A large quantity of orange solid was formed after 2 hours in the refrigerator. It was filtered off and washed with ethanol. Recrystallisation from ethanol afforded 31.53 g of product.

Workup

  1. temperatureThis reaction mixture was refluxed for one hour
  2. waitleft in the refrigerator over the weekend
  3. customA large quantity of orange solid was formed after 2 hours in the refrigerator
  4. filtrationIt was filtered off
  5. washwashed with ethanol
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-38c3cae2d5314cb29705c56f787692e9
Source dataset
uspto-grants-2014_11
Patent number
US08883325B2

Reaction notes

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