m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Conditions

Reaction Steps

26.2 Grams (100 mmoles) of the alphatic diene ester used in Example 1 and 250 ml of methylene chloride were added to a reaction flask, and the resulting solution cooled in an ice bath. 77.8 Grams (270 mmoles) of m-chloroperbenzoic acid was added with stirring in small increments over a period of 15 minutes, while maintaining the temperature of the reaction mixture below 30° C. (25-29° C.) during the addition. The reaction mixture was stirred overnight while allowing the temperature to become room temperature. m-Chlorobenzoic acid precipitate which formed was filtered off, and the filtrate washed twice with 250 ml of 10% aqueous Na2SO3, twice with 350 ml of saturated aqueous NaHCO3 solution, and once with 250 ml of water. The organic layer was separated, dried over MgSO4, and filtered. 50 Grams of basic alumina was then added to the filtrate, the mixture stirred for 45 minutes, and filtered. The methylene chloride solvent was removed under reduced pressure and the product vacuum dried. 26.5 Grams of a crude reaction product was obtained, which was shown by NMR to be significantly contaminated with an aromatic compound by-product.

Provenance & Evidence