Ester hydrolysis (saponification)
5 real reactions from the literature, on esters, malonate esters, five-membered lactones and α,β-unsaturated esters. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Saponification: (4-nitrophenyl)methyl acetate (an ester) with NaOH, Δ; aq. CH3OH gives 4-nitrobenzyl alcohol (the benzylic alcohol).
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Saponification: diethyl 2-benzylpropanedioate (a malonate ester) with 1) KOH; 2) HCl gives benzylmalonic acid (the carboxylic acid).
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Saponification: 2,2,5-trimethyl-5-phenyl-1,3-dioxolan-4-one (a five-membered lactone) with 1); NaOH; 2) HCl / H2O gives atrolactic acid (the carboxylic acid) and acetone (the methyl ketone).
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Saponification: methyl 3-nitrobenzoate (an ester) with 1) aq. NaOH, Δ; 2) HCl gives 3-nitrobenzoic acid (the carboxylic acid).
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Saponification: tert-butyl 2-decylacrylate (an α,β-unsaturated ester) with 1) KOH, CH3CH2OH, Δ; 2) H2SO4, H2O gives 2-decyl acrylic acid (the α,β-unsaturated carboxylic acid).