ChemicalBook CAS DataBase List 4-Nitroanisole

4-Nitroanisole synthesis

13synthesis methods

Product Name:4-Nitroanisole
CAS Number:100-17-4
Molecular formula:C7H7NO3
Molecular Weight:153.14

Produced from p-nitrochlorobenzene by methoxylation.

100-02-7 Synthesis

100-02-7
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$11.00/5G

74-88-4
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$15.00/10g

100-17-4
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$22.00/25g

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

5720-07-0 Synthesis