2-Aminopropanol → HCID 178491096, compound

HRID 716977Notes

Reaction equation

HRID 716977 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-7cb0404f5bc146e78fedc01755c40689
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

Loading…