Veratraldehyde → 39964-87-9

HRID 1501285Notes

Reaction equation

HRID 1501285 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[N:17][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13]

Participants

4

Reactant 2

HCID 8419VeratraldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 1125379939964-87-9Yield 99.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,4-Dimethoxybenzaldehyde (12.20 g, 73.42 mmol) was dissolved in benzene (200 mL) and aminoacetaldehyde dimethyl acetal (12.0 mL, 11.7 g, 111 mmol) was added. The mixture was stirred at reflux for 4 h using a Dean-Stark trap. The reaction mixture was then concentrated and dissolved in CHCl3 (250 mL). The solution was washed with water (4×150 mL) and brine (150 mL), dried (Na2SO4) and concentrated, and the last traces of solvent were removed under vacuum to provide the imine (18.41 g, 99.1%) as a light yellow solid: mp 50-52° C. 1H NMR (300 MHz, CDCl3) δ 8.18 (s, 1H), 7.42 (s, 1H), 7.15 (d, J=8.4 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 4.65 (t, J=5.1 Hz, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.74 (d, J=5.1 Hz, 2H), 3.40 (s, 6H).

Workup

  1. temperatureat reflux for 4 h
  2. concentrationThe reaction mixture was then concentrated
  3. dissolutiondissolved in CHCl3 (250 mL)
  4. washThe solution was washed with water (4×150 mL) and brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customthe last traces of solvent were removed under vacuum

Sources & evidence

ORD record
ord-c48c2591628a4150b983591530e73be7
Source dataset
uspto-grants-2015_12
Patent number
US09206193B2

Reaction notes

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