2-Aminopropanol → HCID 178491096, compound

HRID 1405542Notes

Reaction equation

HRID 1405542 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][CH:12]([CH3:15])[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[N:11]/[CH:12]([CH3:15])[CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 51262-AminopropanolHCID 6101p-Toluenesulfonic acidHCID 312444-Methoxybenzaldehyde

Product 1

HCID 178491096HCID 178491096, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-methoxybenzaldehyde (54.4 g, 400.00 mmol, 1.00 equiv), 2-aminopropan-1-ol (30 g, 400.00 mmol, 1.00 equiv), 4-methylbenzenesulfonic acid (3.84 g, 20.21 mmol, 0.05 equiv), toluene (300 mL). The resulting solution was heated to reflux for overnight in an oil bath. The resulting mixture was concentrated under vacuum. The resulting mixture was washed with 3×50 mL of hexane. The resulting solids were collected by filtration. This resulted in 63 g (82%) of (E)-2-(4-methoxybenzylideneamino)propan-1-ol as a white solid.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for overnight in an oil bath
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. washThe resulting mixture was washed with 3×50 mL of hexane
  7. filtrationThe resulting solids were collected by filtration
  8. customThis resulted in 63 g (82%) of (E)-2-(4-methoxybenzylideneamino)propan-1-ol as a white solid

Sources & evidence

ORD record
ord-732816f20da640bab41a81ee4ced020b
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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