Benzaldehyde → HCID 59047021, compound

HRID 1167872Notes

Reaction equation

HRID 1167872 reaction equation
[OH-].[K+].[CH2:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11](=[O:24])[C:12]3[C:17]([O:18][C:19]=2[C:20]=1[C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:4]=[CH2:5].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.O>[CH2:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11](=[O:24])[C:12]3[C:17]([O:18][C:19]=2[C:20]=1[C:21](=[O:23])[CH:22]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 22994585HCID 22994585, compound

Product 1

HCID 59047021HCID 59047021, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH 50% (3 ml) is added to an equimolar solution of 3-allyloxy-4-acetylxanthen -9one (2.2 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 g of product m.p. 150-152° C., 1H-NMR (CDCl3)δ:4.73-4.74 (m, 2H); 5.25-5.42 (m, 2H); 5.92-6.05 (m, 1H); 7.07 (d, 1H, J=8.9 Hz); 7.13 (d, 1H, J=16 Hz); 7.36-7.44 (m, 6H); 7.52-7.60(m, 2H); 8;31-8.36 (m, 1H); 8.43 (d, 1 H, 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-a5a63c0005604d47b1dcfa2c7be1f4e7
Source dataset
uspto-grants-2003_09
Patent number
US06620842B2

Reaction notes

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