Organic Synthesis O OCH3 O C OH C H NO2

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Presentation transcript:

Organic Synthesis O OCH3 O C OH C H NO2 starting with the aromatic ester methyl benzoate and finishing with the nitro aromatic acid 3-nitro benzoic acid: ester O C OCH3 acid O C OH NO2 H nitro in three separate stages

Stage 1 O C OCH3 O C OCH3 NO2 + HNO3 + H2O Nitration of the aromatic ring to form methyl 3-nitrobenzoate O C OCH3 O C OCH3 NO2 + HNO3 + H2O Cool with concentrated H2SO4

Identification of methyl 3-nitrobenzoate OCH3 NO2 White crystalline solid at room temperature Melting point 77.5 oC Impurities reduce melting point and discolour the solid Compare with 3-nitrobenzoic acid

mass spectrum of methyl 3-nitrobenzoate OCH3 NO2 + m/z relative intensity 75 14 76 24 104 27 150 100 181 23 Mass of molecular ion:181 C6H4(NO2)CO+ C6H4(NO2)COOCH3+ C6H4+ C6H4CO+ Compare with 3-nitrobenzoic acid

Infra red spectrum of methyl 3-nitrobenzoate Compare with 3-nitrobenzoic acid The “finger print” region < 1500 cm-1 C=O 1750 cm-1 unique pattern for each molecule

nmr spectrum of methyl 3-nitrobenzoate nuclear magnetic resonance A B C D E 1H NMR 399.65 MHz C8H7NO4 0.038 g in 0.5 ml CDCl3 Assign. Shift(ppm) A 8.86 B 8.43 C 8.38 D 7.68 E 4.00 Compare with 3-nitrobenzoic acid

Stage 2 O OCH3 O C C + OH - + CH3OH NO2 NO2 Hydrolysis of the ester group to form the 3-nitrobenzoate ion O C OCH3 NO2 O C NO2 + OH - + CH3OH Reflux with concentrated NaOH alkaline hydrolysis

Stage 3 O C NO2 O C OH NO2 + H+ Displacement of weak acid to form 3-nitrobenzoic acid O C NO2 O C OH NO2 + H+ Warm with HCl acid displacement

Identification of 3-nitrobenzoic acid OH NO2 White crystalline solid at room temperature Melting point 141.0 oC Impurities reduce melting point and discolour the solid Compare with methyl 3-nitrobenzoate

mass spectrum of 3-nitrobenzoic acid OH NO2 + m/z relative intensity 65 100 121 44 167 53 Mass of molecular ion:167.0 C6H4(NO2)CO2H+ C6H4(NO2)+ Compare with methyl 3-nitrobenzoate

Infra red spectrum of 3-nitrobenzoic acid Compare with methyl 3-nitrobenzoate The “finger print” region < 1500 cm-1 C=O 1700 cm-1 acid O-H 2600 cm-1 unique pattern for each molecule

nmr spectrum of 3-nitrobenzoic acid 1H NMR 89.56 MHz C7H4NO4 0.025 g in 0.5 ml CDCl3 Assign. Shift(ppm) A 11.67 B 8.96 C 8.49 D 8.47 E 7.74 Compare with methyl 3-nitrobenzoate

References Steve Lewis for the Royal Society of Chemistry Source of the spectral information http://www.aist.go.jp/RIODB/SDBS/menu-e.html