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ChemicalBook CAS DataBase List 4-Nitroanisole
100-17-4

4-Nitroanisole synthesis

13synthesis methods
Produced from p-nitrochlorobenzene by methoxylation.
-

Yield:100-17-4 98%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20;

Steps:


1-Methoxy-4-nitrobenzene asstarting material for the synthesis of 9a:4-Hydroxynitrobenzene(708 mg, 5.1 mmol), K2CO3 (1.62 g, 11.7 mmol)and MeI (1.16 g, 11.7 mmol) were dissolved in DMF (10 ml). The solution wasstirred over night at rt. At the completion of the reaction, water (200 ml)were added to the mixture and it was extracted with Et2O (100 ml)three times. The combined organic layers were dried over Na2SO4,filtered and concentrated under reduced pressure to give the product as a paleyellow solid. Yield: 98 %. C7H7NO3 (Mr 153.0).1H NMR (300 MHz): (CDCl3) d inppm: 3.91 (s, 3H), 6.96 (d, J-9.36Hz, 2H), 8.21 (d, J-9.41 Hz, 2H). 13C NMR (75 MHz): (CDCl3)d in ppm: 55.9, 114.0, 125.9, 141.6, 164.6. MS(EI): m/z 154 [M+H]+.

References:

Schlosser, Joachim;Johannes, Eugen;Zindler, Melanie;Lemmerhirt, Jan;Sommer, Benjamin;Schütt, Martin;Peifer, Christian [Tetrahedron Letters,2015,vol. 56,# 1,p. 89 - 94] Location in patent:supporting information

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