Ethanol → Salicylideneaniline

HRID 58930Notes

Reaction equation

HRID 58930 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-41a44524be644c5bbf2fb2ced05283ad
Source dataset
uspto-grants-2016_09
Patent number
US09437828B2

Reaction notes

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