Pyridine → Methyl 4-chloromethyl-2-nitrobenzoate
Reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.S(Cl)([Cl:18])=O.N1C=CC=CC=1.CCOCC>O1CCCC1>[Cl:18][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methyl 4-hydroxymethyl-2-nitrobenzoate (1.49 g), thionyl chloride (1.08 g), dry pyridine (0.1 g), dry ether (70 ml) and dry tetrahydrofuran (20 ml) was stirred overnight. The reaction mixture was washed in turn with 1N hydrochloric acid and sat. sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give methyl 4-chloromethyl-2-nitrobenzoate (1.60 g).
Workup
- washThe reaction mixture was washed in turn with 1N hydrochloric acid and sat. sodium bicarbonate solution
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-2d1966d1c4134d5eaa2b15dd0f211dc7
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05296487
Reaction notes
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