Benzaldehyde → HCID 85055239, compound

HRID 1884881Notes

Reaction equation

HRID 1884881 reaction equation
[OH-].[K+].[CH3:3][C:4]1[C:13]2[C:8](=[C:9]([C:20](=[O:22])[CH3:21])[C:10]([O:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:11][CH:12]=2)[O:7][C:6](=[O:23])[CH:5]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C.O>[CH3:3][C:4]1[C:13]2[C:8](=[C:9]([C:20](=[O:22])[CH:21]=[CH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]([O:14][CH2:15][CH:16]=[C:17]([CH3:18])[CH3:19])=[CH:11][CH:12]=2)[O:7][C:6](=[O:23])[CH:5]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 23504933HCID 23504933, compound

Product 1

HCID 85055239HCID 85055239, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 4-methyl-7-(3-methylbut-2-enyloxy)-8-acetylcoumarin (2.14 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 ethanol to give 1.34 g of product m.p. 114-16° C., 1H-NMR (CDCl3) δ: 1.69 (s, 3H); 1.72 (s, 3H); 2.44 (d, 3H, J=1.22 Hz); 4.65 (d, 2H, J=6.5 Hz); 5.34-5.38 (m, 1H); 6.16 (d, 1H, J=1.2 Hz); 6.95 (d, 1H, J=8.8 Hz); 7.00 (d, 1H, J=18 Hz); 7.10 (d, 1H); 7.30-7.40 (m, 3H); 7.45-7.52 (m, 12H); 7.61 (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 ethanol

Sources & evidence

ORD record
ord-b64bd0b07d294b0182a5131759d48a3f
Source dataset
uspto-grants-2004_07
Patent number
US06767916B2

Reaction notes

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