3-Methoxybenzaldehyde → HCID 85055237, compound

HRID 1884889Notes

Reaction equation

HRID 1884889 reaction equation
[OH-].[K+].[CH3:3][C:4]1[C:13]2[C:8](=[C:9]([C:18](=[O:20])[CH3:19])[C:10]([O:14][CH2:15][C:16]#[CH:17])=[CH:11][CH:12]=2)[O:7][C:6](=[O:21])[CH:5]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O>C(O)C.O>[CH3:3][C:4]1[C:13]2[C:8](=[C:9]([C:18](=[O:20])[CH:19]=[CH:27][C:26]3[CH:29]=[CH:30][CH:31]=[C:24]([O:23][CH3:22])[CH:25]=3)[C:10]([O:14][CH2:15][C:16]#[CH:17])=[CH:11][CH:12]=2)[O:7][C:6](=[O:21])[CH:5]=1

Participants

6

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 14797Potassium HydroxideHCID 23504931HCID 23504931, compound

Product 1

HCID 85055237HCID 85055237, compoundYield 53.4%

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-prop2-ynyloxy-8-acetylcoumarin (1.92 g, 0.0075 mol) and 3-methoxybenzaldehyde (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 1.5 g of product m.p. 154-56° C., 1H-NMR (CDCl3) δ: 2.45 (s, 3H); 3.48 (m, 1H; 3.81 (s, 3H); 4.82 (d, 2H, J=2.2 Hz); 6.15 (s, 1H); 6.90-7.26 (m, 5H); 7.10 (d, 1H, J=8.9 Hz); 7.65 (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-b20cd5fb284e40978ace06afaf95c1e2
Source dataset
uspto-grants-2004_07
Patent number
US06767916B2

Reaction notes

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