Hydrochloric Acid → 2-Mercapto-6-methylbenzoic acid

Participants

Reaction Steps

5.0 g of 2-amino-6-methylbenzoic acid hydrochloride was converted to a diazonium salt with concentrated hydrochloric acid and 2.3 g of sodium nitrite. Then, this diazonium salt was gradually dropwise added to a previously prepared sodium disulfide solution (which was prepared from 8.7 g of sodium sulfide nonahydrate, 1.1 g of sulfur, 1.5 g of sodium hydroxide and 15 ml of water) at from 0° to 5° C. After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours to complete the reaction. The reaction solution was poured into a large amount of water, and concentrated hydrochloric acid was added thereto. Then, the mixture was extracted with ethyl acetate. A sodium hydrogen carbonate aqueous solution was added to the ethyl acetate layer, and sodium hydrogencarbonate-soluble components were extracted. 5.8 g of sodium pyrosulfate was added to the aqueous solution, and the mixture was refluxed for 30 minutes to complete the reaction. Concentrated hydrochloric acid was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The extract was dried, and then the solvent was distilled off under reduced pressure to obtain 3.6 g (yield: 65%) of 2-mercapto-6-methylbenzoic acid.

Provenance & Evidence