2-methoxy-5-(2-nitroethyl)phenol synthesis

Yield: 68%

Reaction Conditions:

with sodium tetrahydroborate;silica gel in chloroform;isopropyl alcohol at 20; for 0.5 h;

Steps:

4.1.2. General procedure 2 for the synthesis of 2-aryl-1-nitroethanes 4 and 5
General procedure: To a flask containing the corresponding 2-aryl-1-nitroethene were added silica gel (2 g per mmol of starting material), and 1.5 mL of 2-propanol and 8 mL of chloroform per gram of silica gel [53]. To this mixture were added 4 mmol of NaBH₄ per mmol of starting material in small amounts and the resulting mixture was allowed to stir at room temperature until the complete disappearance of the 2-aryl-1-nitroethene (usually noted after a reaction time of about 30 min). The reaction mixture was quenched with an aqueous solution of 0.1 N HCl, filtered to eliminate the silica gel and evaporated under vacuum to eliminate 2-propanol and chloroform. The resulting aqueous mixture was then extracted by CH₂Cl₂ (3×). The organic phase was dried over MgSO₄, filtered and concentrated under vacuum. Crude product was purified by chromatography on silica gel in order to afford the desired compound.

References:

Mur Blanch, Nuria;Chabot, Guy G.;Quentin, Lionel;Scherman, Daniel;Bourg, Stephane;Dauzonne, Daniel [European Journal of Medicinal Chemistry,2012,vol. 54,p. 22 - 32] Location in patent:experimental part