Methanol → Methyl 2-(2-nitrophenyl)acetate
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:12][C:11](=[O:13])[CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]Participants
4
Procedure
A round bottom flask with magnetic stirrer was charged with (2-nitro-phenyl)-acetic acid (10.0 g, 55.0 mmol) and methanol (70 mL) under an argon atmosphere. To the resulting yellow solution at room temperature was added thionyl chloride (12.1 mL, 166 mmol) dropwise via addition funnel (Note: Reaction is very exothermic). The resulting reaction mixture was stirred at room temperature for 12-18 hours and concentrated in vacuo to afford 13.3 g of crude (2-nitro-phenyl)-acetic acid methyl ester as an orange oil. This material was used directly in subsequent reactions.