Synonyms:

Group of substances:

Empirical formula (Hill's system for organic substances):

Structural formula as text:

Molar/atomic mass: 196.269

Synthesis 1:

To a solution of 4-(methylthio)cinnamic acid (10.0 g, 50.0 mol) in methanol (200 mL) at 25 °C, was added magnesium metal turnings (8.5 g, 0.35 mol). [CAUTION: Redistilled, dry methanol must be used, and the temperature of the reaction mixture must be controlled carefully as this reaction is extremely exothermic.] After an induction period of approximately 30 minutes the reaction temperature rose to 55 °C accompanied by a steady evolution of hydrogen gas. After 2 hours the reaction had returned to room temperature where it was poured into a 12N HCl-ice mixture (300 mL) and extracted with ethyl acetate (200 mL, 4x). The organic layers were combined, dried over Na2SO4, and concentrated under reduced pressure, providing a white solid. This material was purified by heating in hexane (375 mL) for 1 hour, followed by hot filtration to remove undissolved solids. The filtrate was concentrated to one half its volume then cooled to 5 °C. After 15 minutes the solid was collected, and washed with cold hexane to provide pure acid (6.56 g, 66% yield), mp 97—99 °C.

R_f 0.49 methylene chloride : methanol (90 : 10).

HRMS calcd. for C10H12O2S (M+): 196.0558. Found: 196.0563.

IR (CHCl3): 3600-2400 (broad), 1715 (strong), 1600 (weak), 1495 (medium), 1440 (medium), 1430 (medium), 1410 (medium), 1300 (medium), 1245 (medium), 1130 (medium), 1090 (medium), 1035 (weak), 1015 (weak), 970 (medium), 955 (medium), 830 (medium), 810 (medium) cm^-1.

1H NMR (CDCl3): δ 2.46 (3H, s), 2.66 (2H, m), 2.91 (2H, m), 7.17 (4H, m), 7.63 (1H, br).

References:

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© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru