Lithium Hydroxide → (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylic acid hydrate

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Reaction Steps

A solution of methyl (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylate (400 mg) in tetrahydrofuran (20 mL) containing 0.5 N aqueous lithium hydroxide solution (4 mL) is stirred at ambient temperature for 2 hours. The reaction is concentrated under reduced pressure and the residue taken up in water. This solution is acidified to pH 1 and extracted with diethyl ether. The organic layer is dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave (E)-3-(2,4-dibenzyloxyphenyl)-2-cyanoacrylic acid hydrate as a yellow solid (30 mg). [Elemental analysis:- C, 71.43; H, 5.25; N, 3.47%; Calculated for C24H19NO4.H2O:- C, 71.40; H, 4.81; N, 3.72%].

Provenance & Evidence