Thionyl Chloride → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate

Participants

Reaction Conditions

Reaction Steps

3,5-Dihydroxybenzoic acid (7.2 g, 50 mM) was dissolved in 11 ml of acetic anhydride. To the resulting solution were added 5 drops of sulfuric acid, followed by stirring at room temperature for 20 minutes. Subsequently, 10 g of ice was added and 12 ml of 1N hydrochloric acid was then added. After sonication, a precipitated crystal was recovered by filtration. Washing the crystal with toluene gave 3,5-diacetoxybenzoic acid (10.23 g). The obtained 3,5-diacetoxybenzoic acid (2.38 g, 10 mM) was dissolved in 5 ml of SOCl2 and the solution was heated under reflux at 80° C. for 1 hour. The solvent SOCl2 was distilled off under reduced pressure to yield 3,5-diacetoxybenzoyl chloride (2.44 g).

Provenance & Evidence