Lithium hydroxide, monohydrate → cis-Cinnamic acid

Participants

Reaction Steps

A solution of (z)-3-phenylpropenoic acid, methyl ester (0.8 g, 4.9 mmol) in 20% aqueous tetrahydrofuran (5 mL) was treated with lithium hydroxide hydrate (0.42 g, 9.9 mmol) and the reaction mixture was stirred under argon at room temperature for 20 hours. It was concentrated in vacuo, diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The organic extracts were discarded and the aqueous layer was acidified to pH~3 with 1N hydrochloric acid and extracted with dichloromethane (3×100 mL). The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title B compound (0.5 g). 1H NMR (CDCl3) δ11.57 (brs, 1H), 7.48 (m, 2H), 7.25 (m, 2H), 6.94 (d, J=12.2 Hz, 1H), 5.84 (d, J=12.3 Hz, 1H).

Provenance & Evidence