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Oxidative coupling of 2-nitrobenzyl chloride; 2,2'-dinitrostilbene

SyntheticPage 622
DOI: 10.1039/SP622
Submitted Jul 12, 2013, published Jul 15, 2013
Max Hammond (max@flipstorm.net), Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: <img src="/images/empty.gif" alt="" />Oxidative coupling of <span id="csm1374250217921" class="csm-chemical-name" title="2-nitrobenzyl chloride">2-nitrobenzyl chloride</span><img src="/images/empty.gif" alt="" />

Chemicals Used

2-nitrobenzyl chloride (Aldrich)
Potassium hydroxide
Ethanol (Fisher Scientific)

Procedure

To 2-nitrobenzyl chloride (5.05 g, 29.43 mmol) in EtOH (20 ml) was added slowly KOH (8.26 g, 148 mmol) in warm EtOH (50 ml) with vigorous stirring. The mixture became warm. The mixture was stirred overnight, and a yellow precipitate was recovered by filtration, washed with EtOH, and recrystallized from ethyl acetate, yielding 2,2’-dinitrostilbene as needle like yellow crystals (1.39 g, 17.5%).

Author's Comments

Low yield in this reaction, but good enough to take forward to next reduction of NO2 step

Data

1H NMR 400 MHz (CDCl3): δ ppm 8.04 (dd, 4JHH = 1 Hz, 3JHH = 8 Hz, 2H, ArH), 7.81 (dd, 4JHH = 1 Hz, 3JHH = 8 Hz, 2H, ArH), 7.67 (td, 4JHH = 1 Hz, 3JHH = 8 Hz, 2H, ArH), 6.57 (s, 2H, CH=CH), 7.48 (td, 4JHH = 1 Hz, 3JHH = 8 Hz, 2H, ArH)

13C{1H} NMR 100 MHz (CDCl3): δ ppm 147.9, 133.7, 132.6, 129.1, 128.9 124.9 (Ar) 130.0 (C=C)

EA: found (calc) C: 62.12 (62.22), H: 3.69 (3.73), N: 10.21 (10.37)

MS (EI+): m/z 270 (M+)


Lead Reference

A. Blanc and C. G. Bochet, J. Org. Chem., 2003, 68, 1138-1141. http://dx.doi.org/10.1021/jo026347x

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Get structure file (.cdx, .sk2, .mol)

Keywords: addition, alkenes, benzyl, chloride, elimination, nitro

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