O-Cresol → 2-(2-Methylphenoxy)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methylphenol (III: R3 =H) (33 g, 305 mmol) in MeOH (100 mL) was treated with Na (2.1 g, 90 mmol), and excess MeOH was removed under reduced pressure. Diphenyliodonium-2-carboxylate (II: R1 =H) (19.6 g, 60 mmol) and cupric acetate (0.5 g) were added and the mixture was stirred at 90° C. for 10 h. The solution was diluted with 2N NaOH, filtered through celite and acidified with HCl. The mixture was then dissolved in 2N K2CO3 and extracted twice with EtOAc to remove excess 2-methylphenol. The aqueous layer was then poured into excess 2N HCl to give 2-(2-methylphenoxy)benzoic acid (IV: R1 =R3 =H) (8.85 g, 64%), suitable for the next step. A sample crystallized from ligroin, mp 133°-134° C. (Ber, 1905, 38, 2111 records mp 133.5° C.).

Provenance & Evidence