Thionyl Chloride → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8]([Cl:20])=[O:9])(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of 3,5-diacetoxybenzoic acid, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3-5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2%.