3-Phenylprop-2-Enal → 953-21-9

HRID 1618325Notes

Reaction equation

HRID 1618325 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8](=O)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)(=O)[C@H](C)O.O>[CH:8](=[N:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 6115Aniline

Product 1

HCID 291034953-21-9

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 92831(L)-ethyl lactateSolvent2×

Procedure

10 mmol aniline was dissolved in approximately 2.5 mL 80% ethyl L-lactate in water (v/v). Separately, 10 mmol of cinnamaldehyde was dissolved in approximately 2.5 mL 80% ethyl L-lactate in water (v/v). The two solutions were combined and the resulting reaction mixture was swirled until homogeneous and then allowed to sit undisturbed at room temperature for four minutes, when crystal formation was complete. Crystals were chilled, rinsed with cold brine and vacuum filtered, washed with cold water, and allowed to air dry. Some of the hydroxyl-containing imines had to be desiccated to completely remove water, especially when humidity was high. All melting points and spectroscopic data were acquired on the crude imines. However, these imines can be recrystallized from ethyl lactate or low molecular weight alcohols.

Workup

  1. customthe resulting reaction mixture
  2. temperatureCrystals were chilled
  3. washrinsed with cold brine and vacuum
  4. filtrationfiltered
  5. washwashed with cold water
  6. customto air dry
  7. additionSome of the hydroxyl-containing imines
  8. customHowever, these imines can be recrystallized from ethyl lactate or low molecular weight alcohols

Sources & evidence

ORD record
ord-57deea2bef0e4c4aad819d8a790b7255
Source dataset
uspto-grants-2014_07
Patent number
US08766004B2

Reaction notes

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