2-Thiocresol → HCID 21162536, compound

Participants

Reaction Conditions

Reaction Steps

In an open flask cuprous oxide (2.25 g., 15.7 mmoles) and o-toluenethiol (3.89 g., 31.4 mmoles) were combined in 40 ml. of dimethylformamide and heated in a 150° C. oil bath until a thick yellow mixture formed. The mixture was cooled slightly and 5-bromofuran-3-carboxylic acid [3.0 g., 15.7 mmoles; Gilman and Burtner, J. Am. Chem. Soc. 55, 2903 (1933)] in 40 ml. of dimethylformamide added. The mixture was heated in a 175° C. oil bath for approximately 16 hours. The reaction mixture was cooled, solids removed by filtration, the filtrate diluted with 500 ml. of water, acidified with 6 N hydrochloric acid and product extracted into three portions of ethyl acetate. The ethyl acetate extracts were combined, evaporated to an oil, the oil taken up in 1 N sodium hydroxide, the basic solution washed with ether, cooled, reacidified and product (650 mg.) recovered by filtration. Recrystallization from methanol/water gave purified 5-(2-methylphenylthio)furan-3-carboxylic acid (485 mg., m.p. 148°-150° C., m/e 234).

Provenance & Evidence