Veratraldehyde → HCID 2852492, compound

HRID 1861576Notes

Reaction equation

HRID 1861576 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][C:15]1[CH:16]=[C:17]([CH2:23][C:24]#[N:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].CC[O-].[Na+]>C(O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:23](=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:24]#[N:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 667273,4-DimethoxybenzeneacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 2852492HCID 2852492, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3,4-dimethoxybenzaldehyde (1.66 g, 100 mmol) and 3,4-dimethoxyphenyl-acetonitrile (1.77 g, 10 mmol) in 50 ml of absolute ethanol, cooled at 0° C. and maintained under nitrogen atmosphere, sodium ethylate (30 mmol) was portionwise added (10 portions, 1 portion/2 min). After complete addition and stirring for further 6 h at room temperature the reaction mixture was cooled to 0° C. and a yellow precipitate occurs. This precipitate was filtered off, washed with ethanol (100 ml) and dried under reduced pressure. This afford the desired stilbene as yellow powder (yield 3 g, 92%).

Workup

  1. temperaturemaintained under nitrogen atmosphere
  2. additionAfter complete addition
  3. temperaturewas cooled to 0° C.
  4. filtrationThis precipitate was filtered off
  5. washwashed with ethanol (100 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ed3c21f0a6df4c869f33add1c6b90b0f
Source dataset
uspto-grants-2003_03
Patent number
US06534135B1

Reaction notes

Loading…