P-Toluic Acid → 4-Methylbenzoyl Chloride

Participants

Reaction Steps

p-Toluic acid (100 g, 0.734 mol) (Tokyo Chemical Industry Co., Ltd.) and toluene (500 mL) (Wako Pure Chemical Industries, Ltd.) were placed into a sufficiently dried recovery flask (egg plant flask), and p-toluic acid was dissolved. Thionyl chloride (132.4 mL, 1.84 mol) (Wako Pure Chemical Industries, Ltd.) was added dropwise to this solution for 1 hour. After the dropwise addition, the solution was heated and refluxed for 2 hours. After the reaction, the temperature was cooled to room temperature, and then remaining thionyl chloride and remaining toluene were evaporated by using a rotary evaporator. Toluene (200 mL) was added to an obtained concentrate, and the concentrating operation was repeated twice. A finally obtained residue was dissolved in tetrahydrofuran (200 mL) (Wako Pure Chemical Industries, Ltd.), which was used in the next step.

Provenance & Evidence