Dichloromethane → Methyl-2-methoxy-4-[(3-oxo-2.3-dihvdrobenzo[b]furan-2-ylidene)methyl]benzoate

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[CH2:2]1.[C:11]([OH:14])(=[O:13])[CH3:12].O=[CH:16][C:17]1[CH:25]=[CH:24]C(O)=[C:19]([O:20][CH3:21])[CH:18]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3].Cl[CH2:32]Cl>>[CH3:32][O:13][C:11](=[O:14])[C:12]1[CH:24]=[CH:25][C:17]([CH:16]=[C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]2=[O:10])=[CH:18][C:19]=1[O:20][CH3:21]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 23556Coumaranone

HCID 9989226Alumina

HCID 20405942HCID 20405942, compound

Product 1

HCID 53765317Methyl-2-methoxy-4-[(3-oxo-2.3-dihvdrobenzo[b]furan-2-ylidene)methyl]benzoate

Procedure

2H-benzofuran-3-one 1 g and vanillin acetate 2.17 g were dissolved in dichloromethane 25 ml, aluminum oxide (manufactured by Merck Co., cat. No. 1076) 24.3 g was added, and the mixture was stirred for 1.5 hours, and aluminum oxide was filtered to obtain a reaction solution. Aluminum oxide was washed with dichloromethane 100 ml three times. This solution and the reaction solution were combined and concentrated at a temperature of 40° C. under reduced pressure. The concentrate was dissolved in methanol 40 ml, the solution was allowed to stand at room temperature for two hours. The precipitated crystals were filtered, and the resulting crystals were dried at a temperature of 60° C. for two hours under reduced pressure to obtain the desired compound 1.44 g.