EAS - Electrophilic Aromatic Substitution Nitration of...

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Electrophilic Aromatic Substitution- Nitration of Aromatics Name : Jordan Gales Teaching Assistant: Mathieu Chellat Lab: T/R 11:30 a.m. – 410 CE Submitted: February 25, 2010 Purpose: To synthesize 1, 2-dimethoxy-4-nitro-benzene via an acid catalyzed electrophilic aromatic substitution reaction between 1, 2-demethoxybenzene and nitric acid. Reaction Scheme : Procedure : 1 A solution of 1, 2-dimethoxybenzene (0.60 g, 4.34 mmol, and 0.55 mL) and glacial acetic acid (1.26 g, 20.96 mmol, 1.20 mL) was cooled to 0°C. A 1:1 mixture of concentrated nitric acid (0.59 g, 9.40 mmol 0.40 mL) and glacial acetic acid (0.42 g, 6.99 mmol, 0.40 mL) was added drop wise for 15 min. After completion of the addition, the mixture was warmed to room temperature (25°C) for 15 min. The reaction mixture was then quenched with crushed ice (5g). The product was then isolated via vacuum filtration and washed with cold water (6.00 mL) and ice cold methanol (6.00 mL). The crude 1, 2-dimethoxy-4-nitro-benzene product was then
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EAS - Electrophilic Aromatic Substitution Nitration of...

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