4-(methylthio)cinnamic acid

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Properties of substance:

4-(methylthio)cinnamic acid

skc-file

Group of substances:

organic

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

C₁₀H₁₀O₂S

Structural formula as text:

CH3SC6H4CH=CHCOOH

Molar/atomic mass: 194.253

Synthesis 1:

Reference: Heffner, R. J., & Joullie, M. M. Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin / Synthetic Communications. - 1991. - Vol. 21, No. 21 pp. 2249-2250 [doi: 10.1080/00397919108055457]

A solution of 4-(methylthio)benzaldehyde (50.0 g, 0.328 mol), malonic acid (51.2 g, 0.492 mol), pyridine (31.2 mL, 0.834 mol) and piperidine (1 mL) as catalyst was heated at 110 °C for 5 hours. After this time the reaction was diluted with ethyl ether (450 mL) and cooled in an ice bath for 1 hour whereupon a solid precipitated. This material was collected by filtration and rinsed with ethyl ether. The filtrate was washed with 2N HCl (100 mL, 2x), whereupon more solid precipitated, and was removed by filtration. The filtrate was extracted with 5% NaHCO3 solution (100 mL, 3x) and upon re-acidification of the aqueous extract, additional product precipitated and was collected. All solid portions were combined, providing the acid (58 g, 91% yield). The product was purified by recrystallization from acetonitrile affording pure acid, mp 173—175 °C, lit mp 170—171 °C.

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

HRMS calcd. for C10H10O2S (M+): 194.0401. Found: 194.0400.

IR (KBr): 3500-2000 (broad), 1690 (strong), 1620 (strong), 1590 (strong), 1550 (weak), 1490 (medium), 1430 (medium), 1310 (medium), 1280 (medium), 1220 (medium), 1180 (medium), 1080 (medium), 975 (medium), 940 (medium), 910 (medium), 705 (medium) cm^-1.

1H NMR (DMSO-d6): δ 2.50 (3H, s), 6.49 (1H, d, J = 16 Hz), 7.27 (2H, d, J = 8.5 Hz), 7.56 (1H, d, J = 16 Hz), 7.63 (2H, d, J = 8.5 Hz), 12.3 (1H, br).

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