Toluene → 4-(2-Phenylethenyl)benzoyl chloride
Reaction equation
[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7](O)=[O:8])=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O.C1(C)C=CC=CC=1>CN(C)C=O>[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]([Cl:20])=[O:8])=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
15.1 g (67.4 mmols) of stilbene-4-carboxylic acid, 10.0 g (84.25 mmols) of thionyl chloride, 150 ml of toluene and 0.18 ml of N,N-dimethylformamide are stirred at 70° C. for 3 hours. The reaction mixture is then evaporated and the crude product is recrystallised from n-hexane/cyclohexane. 13.7 g (84% of theory) of stilbene-4-carboxylic acid chloride are obtained in the form of white crystals; melting point 131.2° C.