Potassium Carbonate → 2-((2-Methoxyethoxy)methoxy)-3-nitrobenzoic acid methyl ester

HRID 912428Notes

Reaction equation

HRID 912428 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[OH:13].C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[O:13][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 582228052-((2-Methoxyethoxy)methoxy)-3-nitrobenzoic acid methyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-3-nitrobenzoic acid methyl ester 9.9 g (50 mmol) in dimethylformamide 100 mL were added K2CO3 7.6 g (55 mmol) and chloromethoxyethoxymethane 6.3 mL (55 mmol), followed by stirring at room temperature for 2 hrs. The resulting reaction mixture was concentrated in a vacuum, diluted with ethylacetate and washed with distilled water and a saturated NaCl solution. The residue was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound 14.0 g (yield 98%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated in a vacuum
  3. additiondiluted with ethylacetate
  4. washwashed with distilled water
  5. dry with materialThe residue was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-700288f284454a8699fe4a83b08a7606
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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