ChemicalBook CAS DataBase List 3,4-DIMETHOXY-B-NITROSTYRENE

3,4-DIMETHOXY-B-NITROSTYRENE synthesis

7synthesis methods

Product Name:3,4-DIMETHOXY-B-NITROSTYRENE
CAS Number:4230-93-7
Molecular formula:C10H11NO4
Molecular Weight:209.2

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120-14-9 Synthesis

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4230-93-7
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Yield: 97%

Reaction Conditions:

with ammonium acetate in acetic acid at 90 - 100; for 1 h;Molecular sieve;Henry Nitro Aldol Condensation;

Steps:

Method A: General procedure for nitroaldol reaction
General procedure: Aldehyde (4 mmol) was added to a round bottomflask containing a solution of 0.3 g (4 mmol, 1 eq.) of ammonium acetate (fresh commercial solid workswell, however it must be recrystallized from glacial acetic acid if it appears wet) dissolved in 1.1 mL (20mmol, 5 eq.) of nitromethane, 3.0 mL (56 mmol, 14 eq.) of glacial acetic acid, and small number of 3?molecular sieves. The flask was attached to a condenser with septum and the assembly was loweredinto a sand bath. The reaction mixture was allowed to gently reflux at 90-100 °C with stirring for onehour. After removing the molecular sieves, the resulting bright yellow solution was partitioned between10 mL of brine and extracted with 3 x 25 mL portions of ethyl acetate. Organic extracts were combinedand rinsed with 3 X 50 mL portions of deionized water, dried over MgSO4, vacuum filtered, andconcentrated under vacuum to afford a dense yellow crystalline solid. Unless otherwise specified, allisolated products were free of starting material, side products, and ammonium acetate by 1H-NMR and HPLC-UV. If further purification is required due to the presence of minor side products, the nitrostyrenemay be recrystallized by dissolving in minimal methanol and adding distilled water at room temperature.All reported melting points were from crude isolated solid.

References:

Maresh, Justin J.;Ralko, Arthur A.;Speltz, Tom E.;Burke, James L.;Murphy, Casey M.;Gaskell, Zachary;Girel, Joann K.;Terranova, Erin;Richtscheidt, Conrad;Krzeszowiec, Mark [Synlett,2014,vol. 25,# 20,art. no. ST-2014-S0514-1,p. 2891 - 2894] Location in patent:supporting information

75-52-5
0 suppliers
$31.19/100g

120-14-9 Synthesis

120-14-9
818 suppliers
$5.00/25g