Toluene → 2-Methylbenzoic acid

Participants

Reaction Steps

Trifluoroacetic acid (5 mL) was added to RhCl3.nH2O (10 mg). To this suspension (the Rh complex was insoluble), K2S2O8 (1.40 g) was added, and the mixture was stirred in air for 15 minutes. After toluene (5 mL) was added, the mixture was stirred under CO for 24 hours, and then analyzed by GC-MS, in a usual manner (see above), with chlorobenzene as an internal standard. No toluic acid formed. When the rhodium chloride-catalyzed reaction was run for 61 hours under similar conditions, about 185 mg of p-toluic acid formed (TON=38).

Provenance & Evidence