3-(Methylthio)benzoic acid

Methyl iodide (0.972 mL) was added to a mixture of 3-mercapto-benzoic acid (601 mg, 3.9 mmol) and potassium carbonate (2.7 g, 19.5 mmol) in DMF (8 mL) in an ice-bath. After the reaction was warmed to room temperature and stirred for 1 hour, the reaction mixture was diluted with ethyl acetate, washed with water (3X), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid methyl ester (684 mg, 96percent, yellow [OIL). 1H] NMR [(CDC13), ] [S] (ppm): 7.90 (s, 1H), 7.80 (d, [1H), ] 7.44 (d, 1H), 7.35 (t, 1H), 3.92 (s, 3H), 2.53 (s, 3H). 3-Methylsulfanyl-benzoic acid methyl ester (684mg, 3.8 mmol) and 1N [NAOH] (5.6 mL, 5.6 mmol) in methanol (8 [ML)] and THF (8 mL) were heated at [70°C] for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. After acidification with 1N [HC1] to [PH-2, ] the aqueous layer was extracted with ethyl acetate and then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid (616 mg, 97percent, white [SOLID). 1H] NMR (DMSO), [8] (ppm): 13.1 (bs, [1H), ] 7.76 (s, 1H), 7.70 (d, 1H), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).3-Methylsulfanyl-benzoic acid methyl ester (684 mg, 3.8 mmol) and [1N NAOH] (5.6 mL, 5.6 mmol) in methanol (8 [ML)] and THF (8 mL) were heated at [70°C] for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. After acidification with 1N [HC1] to [PH-2, ] the aqueous layer was extracted with ethyl acetate and then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford [3-METHYLSULFANYL-BENZOIC] acid (616 mg, 97percent, white [SOLID). LHNMR (DMSO), 6] (ppm): 13. 1 (bs, [1H), ] 7.76 (s, 1H), 7.70 (d, 1H), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).The aminobenzoic acid (54.8 g, 0.4 mol) was diazotized in the usual manner with sodium nitrite (27.6 g, 0.4 mol) and hydrochloric acid (40 mL) and the resulting diazonium salt solution poured into a hot (70° C.), freshly prepared solution of potassium ethyl xanthate (64.2 g, 0.4 mol) containing sodium carbonate (55.2 g, 0.4 mol) to neutralize acid in the diazonium salt solution.

Molecular Weight:168.21
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:168.02450067
Monoisotopic Mass:168.02450067
Topological Polar Surface Area:62.6
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes