Water → 10-(Propylthio)decanoic acid

Participants

Reaction Conditions

Reaction Steps

10-bromodecanoic acid (1.0 g, 3.98 mmol) was added to a solution of potassium hydroxide (0.893 g, 15.9 mmol) in 1-propanethiol (30 mL) and methanol (30 mL) and stirred at 69° C. for 18 hrs. The reaction was allowed to cool to room temperature after the addition of 20 mL water. After acidification to pH=1 and extraction into ethyl acetate, the organic phase was dried over sodium sulfate and solvent removed at reduced pressure to yield a white crystalline powder. The product was purified by silica column chromatography in 8% ethyl acetate/hexane/0.3% formic acid and recrystallization from hexane to yield 10-(propylthio)decanoic acid (210 mg, 21%), mp 42°-43.5° C.; 1H NMR (300 MHz, CDCl3) δ0.96 (t, 3H, J=7.3, CH3) 1.15-1.40 (bm, 10H, methylene envelope), 1.49-1.64 (bm, 6H, CH3CH2CH2SCH2CH2, CH2CH2COOH), 2.32 (t, 2H, J=7.6, CH2COOH), 2.40-2.55 (bm, 4H, CH3CH2CH2SCH2), 10.93 (Br, 1H, COOH); 13C NMR (75.4 MHz, CDCL3) δ 13.64, 23.09, 24.71, 28.96, 29.07, 29.13, 29.24, 29.36, 29.77, 32.16, 34.10, 34.28, 179.98; m/z 247 (M+H).

Provenance & Evidence