3-Thiophen-2-ylprop-2-enoic acid → 3-(2-Thienyl)propanoic acid

Participants

Reaction Steps

Palladium on carbon (10%, 4.2 g) was added in one portion to a solution of 3-(2-thienyl)acrylic acid (15.59 g, 0.10 mol) in tetrahydrofuran (130 mL). The mixture was subjected to Parr hydrogenation conditions (45 psi, room temperature) for about 24 hours. Following filtration through Celite, the filtrate was concentrated down to dryness and gave a brown-colored solid which was recrystallized from water. There was isolated 9.32 g (60%) of the title compound as a mixture of white and tan colored needles, m.p. 58°-60° C. (m.p. lit. 62°-62.5° C.); 1H NMR (CD3SOCD3) 6 12.2 (br s, 1H), 7.23-7.21 (m, 1H), 6.89-6.86 (m, 1H), 6.82-6.81 (m, 1H), 2.99 (t, J=7.4 Hz, 2H), 2.53 (t, J=7.4 Hz, 2H); 13C NMR (CD3SOCD3) ppm 173.42, 143.39, 126.90, 124.70, 123.72, 35.61, 24.70; IR (KBr, cm-1) 3102-3036, 2922, 2644, 1706, 1440, 1408, 1310, 1232, 1220, 938, 848, 828, 714, 692; MS m/z (MH+) 157.

Provenance & Evidence