Hydrochloric Acid → 4-Methoxymethyl-2-nitrobenzoic acid

HRID 487596Notes

Reaction equation

HRID 487596 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.[CH3:16][O-:17].[Na+].CO.O.Cl>CO>[CH3:16][O:17][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19092337Methyl 4-chloromethyl-2-nitrobenzoateHCID 23694274Sodium methanolate methanol

Product 1

HCID 190923184-Methoxymethyl-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-chloromethyl-2-nitrobenzoate (1.6 g), 28% sodium methoxide-methanol solution (2.5 ml) in methanol (16 ml) was stirred under reflux for 24 hours. To this mixture, water (5 ml) was added and the mixture was stirred for 2 hours, acidified with 1N hydrochloric acid, extracted with ethyl acetate. The combined organic extract was washed with water, dried over magnesium sulfate and evaporated to give 4-methoxymethyl-2-nitrobenzoic acid (0.84 g).

Workup

  1. temperatureunder reflux for 24 hours
  2. stirringthe mixture was stirred for 2 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-244636acb22c4a39a1874d387d52cc69
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

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