Sodium Methoxide → HCID 23144869, compound

HRID 1393065Notes

Reaction equation

HRID 1393065 reaction equation
C[O-].[Na+].Br[CH2:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].[O:19]1CCOC[CH2:20]1.Cl>CO>[CH3:20][O:19][CH2:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 204431481,4-Dioxane hydrochlorideHCID 22509333Methyl 3-(bromomethyl)-2-nitrobenzoate

Product 1

HCID 23144869HCID 23144869, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol solution (4.7 mL) of sodium methoxide (197 mg) was added dropwise into the mixture of methyl 3-bromomethyl-2-nitrobenzoate (1 g) and methanol (7 mL) under heating and refluxing. Two minutes later, the mixture was cooled down with ice and 1.82 mL of 4M hydrogen chloride dioxane solution was added dropwise thereto. After removing the solvent, diethylether and water were added and the organic layer thereof was dried over sodium sulfate. After removing the solvent, the obtained residue was purified with silica gel column chromatography to obtain 621 mg of methyl 3-methoxymethyl-2-nitrobenzoate.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. additionwas added dropwise
  4. customAfter removing the solvent, diethylether and water
  5. additionwere added
  6. dry with materialthe organic layer thereof was dried over sodium sulfate
  7. customAfter removing the solvent
  8. customthe obtained residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-950fb1c4009f4becac0f69404b81060e
Source dataset
uspto-grants-2008_03
Patent number
US07345049B2

Reaction notes

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