Methanol → HCID 14801183, compound

Reaction equation

[Na].[CH3:2][C:3]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[Li+].[I-].[CH3:16][OH:17]>>[CH3:2][C:3]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][O:17][CH3:16]

Participants

Reactant 4

HCID 887Methanol

HCID 66321Lithium iodide

HCID 108947alpha-Chloro-2-methyl-3-nitrotoluene

HCID 5360545Sodium

Product 1

HCID 14801183HCID 14801183, compoundYield 92%

Procedure

To a solution of sodium (0.10 g, 4.3 mmol) in methanol (40 ml) was added 2-methyl-3-nitrobenzylchloride (0.50 g, 2.7 mmol) and catalytic amounts of LiI under nitrogen. After the reaction occurred at 40° C. over night, the solvent evaporated and the residue was purified by chromatography (heptane/EtOAc) to give the title compound 450 mg, (92%) as a yellow oil.