ChemicalBook CAS DataBase List 4-Methyl-2-nitroanisole

4-Methyl-2-nitroanisole synthesis

12synthesis methods

Product Name:4-Methyl-2-nitroanisole
CAS Number:119-10-8
Molecular formula:C8H9NO3
Molecular Weight:167.16

119-33-5
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$23.00/25g

77-78-1
318 suppliers
$19.69/1ml

119-10-8
145 suppliers
$10.00/1g

Yield: 90%

Reaction Conditions:

Stage #1:4-methyl-2-nitrophenol with sodium hydroxide in water
Stage #2:dimethyl sulfate with tetrabutylammomium bromide in dichloromethane;water at 10 - 25; for 10 - 12 h;

Steps:

3.2
Step 2: 4-Methyl-2-nitrophenol methyl ether; 4-Methyl-2-nitrophenol (1 equivalent) was dissolved in a solution of NaOH (1.5 equivalent) in water (10 times) to form the sodium salt. Tetrabutyl ammonium bromide (0.05 equivalents) and dichloromethane (10 times) were then added and the resulting mixture was cooled at 1O⁰C. To this, dimethyl sulfate (1.2 equivalent) was added was drop wise and the resulting reaction mixture was stirred at 25⁰C for 10- 12h. After completion, the organic layer was separated and the aqueous layer was EPO extracted with dichloromethane. The organic extracts were combined and washed with water, brine and dried over anhydrous Na₂SO₄. The solvent was removed by distillation under vacuum to yield the crude product which was column chromatographed using 20 % ethyl acetate in petroleum ether to give yellow oil. Yield: 90%IR (KBr): 2965, 2846, 2878, 1728, 1623, 1529, 1462, 1350, 1261, 1200, 1158, 1061, 1020, 921, 883, 852, 810, 766, 672, 593.¹H NMR (300 MHz, DMSO): 2.307 (s, 3H), 3.88 (s, 3H), 7.257 (d, IH, J - 8.4Hz), 7.492 (d, IH, J= 8.7 Hz), 7.693 (s, IH) M⁺¹: 168

References:

GLENMARK PHARMACEUTICALS S.A. WO2006/40650, 2006, A1 Location in patent:Page/Page column 31-32

104-93-8 Synthesis