Pyridine → Methyl 4-chloromethyl-2-nitrobenzoate

HRID 487595Notes

Reaction equation

HRID 487595 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]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoate

Product 1

HCID 19092337Methyl 4-chloromethyl-2-nitrobenzoateYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. washThe reaction mixture was washed in turn with 1N hydrochloric acid and sat. sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-2d1966d1c4134d5eaa2b15dd0f211dc7
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

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