4-Methoxybenzenethiol → HCID 13689101, compound

Participants

Reaction Conditions

Reaction Steps

An ice-cooled suspension of 3.0 g (0.125 mol) of oil-free sodium hydride in 100 ml of tetrahydrofuran was treated portionwise during ten minutes with 12.2 g (0.052 mol) of 2,6-dichloro-3-nitrobenzoic acid [Lehmstedt and Schrader, Ber. 70B, 1526 (1937)]. After stirring for ten minutes, the suspension was treated dropwise with 7.0 g (0.05 mol) of 4-methoxybenzenethiol [C. M. Suter and H. L. Hansen, J. Am. Chem. Soc., 54, 4100 (1934)] in 50 ml of tetrahydrofuran. After stirring for 30 minutes at 0° C., the cooling bath was removed and the mixture was maintained at 25° C. for 12 hours. The mixture was acidified with 150 ml of 10% aqueous HCl, then treated with 200 ml of ethyl acetate. The organic layer was separated and the aqueous phase was extracted with 100 ml of ethyl acetate. The combined organic phases were dried (MgSO4), and concentrated to a yellow solid which was purified by flash chromatography on silica gel, utilizing dichloromethane:methanol (8:1) as eluting solvent, to give 11.9 g of 6-chloro-2-[(4-methoxyphenyl)thio]-3-nitrobenzoic acid, mp 154°-157° C., following crystallization from toluene.

Provenance & Evidence