Ethanol → HCID 59094099, compound

HRID 1167878Notes

Reaction equation

HRID 1167878 reaction equation
[OH-].[K+].[CH3:3][C:4](=[CH2:28])[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:24])[C:12]([CH3:23])=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14]2)=[C:9](C(=O)C)[CH:8]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH:34]=O.[CH2:39]([OH:41])[CH3:40]>O>[CH3:23][C:12]1[C:11](=[O:24])[C:10]2[C:15](=[C:16]([C:39](=[O:41])[CH:40]=[CH:34][C:33]3[CH:36]=[CH:37][CH:38]=[C:31]([O:30][CH3:29])[CH:32]=3)[C:7]([O:6][CH2:5][C:4]([CH3:3])=[CH2:28])=[CH:8][CH:9]=2)[O:14][C:13]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 115693-MethoxybenzaldehydeHCID 14797Potassium HydroxideHCID 69979331HCID 69979331, compound

Product 1

HCID 59094099HCID 59094099, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 7-(2-methylallyloxy) -acetyl-3methylflavone (2.61 g, 0.0075 mol) and 3-methoxy-benzaldehyde (1.01 g, 0.0075 mol) in ethanol 95%; the addition is performed under energetic stirring at room temperature. The reaction is left under stirring for one night and then diluted with water and acidified; the precipitate is separated by filtration and dried under vacuum. The compound is crystallized by methanol to give 2.4 g of product m.p. 131-34° C., 1H-NMR (CDCl3)δ:1.76 (s, 3H); 2.20 (s, 3H); 3.82 (s, 3H) 4.62 (s, 2H); 5.05 (d, 2H, J=18 Hz); 6.95-7.10 (m, 3H); 7.09 (d, 1H, J=9 Hz); 7.10 (d, 1H, J=9 Hz); 7.31 (d, 1H, J=16 Hz); 7.40-07.45 (m, 3H); 7.55-7.58 (m, 2H); 7.31 (s, 2H); 8.32 (d, 1H, J=8.9 Hz).

Workup

  1. additionthe addition
  2. waitThe reaction is left
  3. stirringunder stirring for one night
  4. customthe precipitate is separated by filtration
  5. customdried under vacuum
  6. customThe compound is crystallized by methanol

Sources & evidence

ORD record
ord-de2a90b343b040cb9a475b92b745e408
Source dataset
uspto-grants-2003_09
Patent number
US06620842B2

Reaction notes

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