Salicylaldehyde → 4-(2-Hydroxybenzylideneamino)-3-methylphenol

HRID 434716Notes

Reaction equation

HRID 434716 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH:10](=O)[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13].C(OCC)(=O)C>CCCCCC>[OH:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=1[CH:10]=[N:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8857Ethyl AcetateHCID 178194-Amino-m-cresol

Product 1

HCID 2806574-(2-Hydroxybenzylideneamino)-3-methylphenolYield 93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer and drying tube was added 12.32 grams (0.10 mole) of 4-amino-3-methylphenol, 12.21 grams (0.10 mole) of salicylaldehyde and 250 milliliters of ethyl acetate. The resulting reaction mixture was stirred for 19 hours at room temperature and ambient pressure. After the stirring period, the reaction mixture was washed twice with saturated brine solution and decolorized with activated charcoal. The reaction mixture was then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a yellow oil which solidified on standing. The resulting solidified material was slurried in hexane, collected by filtration and dried to yield 21.12 grams (0.093 moles) of 4-(2-hydroxybenzylideneamino)-3-methylphenol in the form of a yellow solid having a melting point of 95°-97° C.

Workup

  1. customTo a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer
  2. customdrying tube
  3. customThe resulting reaction mixture
  4. washAfter the stirring period, the reaction mixture was washed twice with saturated brine solution
  5. dry with materialThe reaction mixture was then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil which
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-eb11a3c163ae48ae8310b1b6227b24fa
Source dataset
uspto-grants-1983_08
Patent number
US04399148

Reaction notes

Loading…