Hydrochloric Acid → 1-(Methoxymethyl)-2-nitrobenzene

HRID 1421376Notes

Reaction equation

HRID 1421376 reaction equation
[CH3:1][O-:2].[Na+].[N+:4]([C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]Br)([O-:6])=[O:5].Cl>CO>[CH3:1][O:2][CH2:9][C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[N+:4]([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 77569alpha-Bromo-2-nitrotolueneHCID 10942334Sodium Methoxide

Product 1

HCID 126166891-(Methoxymethyl)-2-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

125 g of 30% strength sodium methylate solution (0.69 mol) in methanol are added dropwise to 130 g (0.6 mol) of o-nitrobenzyl bromide in 200 ml of methanol. During this procedure, the reaction mixture heats up to about 50° C. Stirring is continued for a further 3 hours, the reaction mixture being cooled to room temperature, after which ice water is added to the reaction vessel and the reaction mixture is neutralized by adding dilute hydrochloric acid. The aqueous phase is extracted with three times with ether, and the organic phase is dried over MgSO4 and evaporated down. 101 g (0.6 mol, quantitative yield) of the title compound are obtained as a residue in the form of a brownish oil.

Workup

  1. customheats up to about 50° C
  2. extractionThe aqueous phase is extracted with three times with ether
  3. dry with materialthe organic phase is dried over MgSO4
  4. customevaporated down

Sources & evidence

ORD record
ord-740da360304f42bdaba4fdb660147198
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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