Benzaldehyde → HCID 86587444, compound

HRID 1167880Notes

Reaction equation

HRID 1167880 reaction equation
[OH-].[K+].[CH2:3]([O:6][C:7]1[C:16](C(=O)C)=[C:15]2[C:10]([C:11](=[O:27])[C:12]([CH3:26])=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:14]2)=[CH:9][CH:8]=1)[C:4]#[CH:5].[CH:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH2:36](O)[CH3:37]>O>[CH3:26][C:12]1[C:11](=[O:27])[C:10]2[C:15](=[C:16]([C:29]3([C:28](=[O:35])[CH:36]=[CH2:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH2:30]3)[C:7]([O:6][CH2:3][C:4]#[CH:5])=[CH:8][CH:9]=2)[O:14][C:13]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 14797Potassium HydroxideHCID 17906104HCID 17906104, compound

Product 1

HCID 86587444HCID 86587444, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 7-(prop-2-ynyloxy) -8-acetyl-3-methylflavone (2.49 g, 0.0075 mol) and benzaldehyde (0.8 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 2.8 g of product m.p. 157-59° C., 1H-NMR (CDCl3)δ: 2.20 (s, 3H); 2.56 (s, 1H); 4.86 (d, 2H, J=2.2 Hz); 7.05 (d, 1H, J=16 Hz); 7.23 (d, 1H, J=8.9 Hz); 7.31-7.50 (m, 7H); 7.50-7.57 (m, H); 8,34 (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-cfc30a56b36040238723096a81868b23
Source dataset
uspto-grants-2003_09
Patent number
US06620842B2

Reaction notes

Loading…