2-Butylbenzofuran → 2-n-Butyl-3-(3'-methyl-4'-methoxybenzoyl)benzofuran
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](Cl)=[O:6].[CH2:13]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[CH:21]=1)[CH2:14][CH2:15][CH3:16]>C(=S)=S>[CH2:13]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[C:21]=1[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([CH3:1])[CH:3]=1)[CH2:14][CH2:15][CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled, stirred solution of 10.8 g. (0.058 mol.) of 3-methyl-4-methoxybenzoic acid chloride and 9.4 g. (0.054 mol.) of 2-n-butylbenzofuran in 40 ml. of carbon disulfide was added dropwise over a 20 minute interval 28.2 g. (0.108 mol.) of stannic chloride. After addition, the reaction mixture was warmed to ambient temperature and stirred for two hours. The mixture was then poured onto 100 ml. of ice-water and stirred for one hour. The solvent was removed, the product extracted into chloroform and the extracts were washed with water, dried (Na2SO4) and concentrated in vacuo to give 2-n-butyl-3-(3'-methyl-4'-methoxybenzoyl)benzofuran.