3-Methoxybenzaldehyde → HCID 59047019, compound

HRID 1167870Notes

Reaction equation

HRID 1167870 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH3:26])=[CH:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12](=[O:25])[C:13]3[C:18]([O:19][C:20]=2[C:21]=1[C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=[CH:15][CH:14]=3.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O>C(O)C.O>[CH3:3][C:4]([CH3:26])=[CH:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12](=[O:25])[C:13]3[C:18]([O:19][C:20]=2[C:21]=1[C:22](=[O:24])[CH:23]=[CH:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([O:28][CH3:27])[CH:30]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

6

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 14797Potassium HydroxideHCID 22994580HCID 22994580, compound

Product 1

HCID 59047019HCID 59047019, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 3-(3-methylbut -2-enyloxy)4acetylxanthen-9one (2.4 g, 0.0075 mol) and 3-methoxy-benzaldehyde (1.01 g, 0.0075 mol) in ethanol 95%, the addition being 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 with methanol to give 1.9 g of product m.p. 134-36° C., 1H-NMR (CDCl3) δ: 1.69 (s, 3H); 1.72 (s, 3H); 3.84 (s, 3H); 4.71 (d, 2H, J=6.5); 5.38-5.40 (m, 1H); 6.95-6.98 (m, 1H); 7.05-7.15 (m, 2H); 7.08 (d, 1H, J=8.8 Hz); 7.09 (d, 1H, J=16 Hz); 7.23-7.42 (m, 4H); 7.65-7.72 (m, 1H); 8.32-8 (d, 1H. J=8.8 Hz); 8.42(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 with methanol

Sources & evidence

ORD record
ord-cc181abf36134ab1b7d92779b2a3edc4
Source dataset
uspto-grants-2003_09
Patent number
US06620842B2

Reaction notes

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