ChemicalBook CAS DataBase List p-Nitrophenylacetonitrile

p-Nitrophenylacetonitrile synthesis

10synthesis methods

Product Name:p-Nitrophenylacetonitrile
CAS Number:555-21-5
Molecular formula:C8H6N2O2
Molecular Weight:162.15

140-29-4
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$18.00/25mL

555-21-5
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$21.00/25g

Yield:555-21-5 88%

Reaction Conditions:

with sulfuric acid;nitric acid at 10 - 20; for 1 h;

Steps:

5.1.9. 2-(4-Nitrophenyl)acetic acid (32
)A mixture of concentrated nitric acid (1.47 mL) and an equal volumeof concentrated sulphuric acid (1.47 mL) was placed in a two neckflask fitted with a thermometer and a dropping funnel. The mixture wascooled to 10 °C in ice bath and benzyl cyanide (1.0 g, 8.53 mmol) wasrun at such a rate that the temperature was maintained around 10 °Cand did not rise above 20 °C. The solution was further stirred for 1 h atroom temperature and then poured into crushed ice. The mass wasfiltered under vacuum and pressed well to remove as much oil as possible.The crude product was recrystallize from methanol to obtain 2-(4-nitrophenyl)acetonitrile (yield:1.21 g, 88%); m.p. 110-112 °C (lit. [55]m.p. 113-115 °C); IR (KBr, cm-1): 3117, 3054, 2943, 2851, 2253,1517, 1345, 1107, 732. A solution of sulphuric acid (50%) was preparedby adding concentrated sulphuric acid cautiously to water. Twothird of the sulphuric acid was added into a round bottom flask containing2-(4-nitrophenyl)acetonitrile (1.0 g) and the nitrile adhering tothe walls of the flask was washed down with the remaining acid. Thecontent was boiled under reflux for 15 min and diluted with 25 mL ofice-cold water. The resulting pale yellow solid mass was filtered, washed,decolorized and recrystallized from hot water to yield titledcompound (32) (yield: 0.87 g, 78%); m.p. 148-150 °C (lit [55] m.p.151-152 °C); IR (KBr, cm-1): 3450, 3084, 2931, 2847, 1708, 1514,1346, 951, 709.

References:

Chaudhary, Bharat N.;Gandhi, Pallav M.;Joshi, Prashant D.;Kanhed, Ashish M.;Patel, Dushyant V.;Patel, Kirti V.;Patel, Kishan B.;Patel, Nirav R.;Patel, Sagar P.;Prajapati, Navnit K.;Teli, Divya M.;Yadav, Mange Ram [Bioorganic Chemistry,2020,vol. 101]

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