4-Chlorobenzaldehyde → HCID 59094093, compound

HRID 1167882Notes

Reaction equation

HRID 1167882 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH3:29])=[CH:5][CH2:6][O:7][C:8]1[C:17]([C:18](=[O:20])[CH3:19])=[C:16]2[C:11]([C:12](=[O:28])[C:13]([CH3:27])=[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:15]2)=[CH:10][CH:9]=1.[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1>C(O)C.O>[CH3:27][C:13]1[C:12](=[O:28])[C:11]2[C:16](=[C:17]([C:18](=[O:20])[CH:19]=[CH:35][C:34]3[CH:37]=[CH:38][C:31]([Cl:30])=[CH:32][CH:33]=3)[C:8]([O:7][CH2:6][CH:5]=[C:4]([CH3:29])[CH3:3])=[CH:9][CH:10]=2)[O:15][C:14]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 22994576HCID 22994576, compound

Product 1

HCID 59094093HCID 59094093, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 7-(3-methylbut-2-enyloxy)-8-acetyl-3-methylflavone (2.71 g, 0.0075 mol) and 4-chloro-benzaldehyde (1.05 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 1.9 g product m.p. 130-133° C., 1H-NMR (CDCl3) δ:1.69 (s, 3H), 1.72 (s, 3H), 2.19 (s, 3H), 4.65 (d. 2H), 5.31 (m, 1H), 6.97-8.42 (m, 13H).

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-eb88226e6fc5443097288ae6e8507ea6
Source dataset
uspto-grants-2003_09
Patent number
US06620842B2

Reaction notes

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