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

HRID 1809130Notes

Reaction equation

HRID 1809130 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

9.9 g (50 mmol) of 2-hydroxy-3-nitrobenzoic acid methyl ester was dissolved in 100 mL of dimethylformamide. 7.6 g (55 mmol) of K2CO3 and 6.3 mL (55 mmol) of chloromethoxyethoxymethane were added thereto and stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, followed by dilution with ethyl acetate and washing with distilled water and saturated sodium chloride solution. The resulting residue was dried over magnesium sulfate and concentrated under reduced pressure to obtain the title compound (14.0 g, yield: 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashing with distilled water and saturated sodium chloride solution
  3. dry with materialThe resulting residue was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0db3811871d480ba610292ef9464f09
Source dataset
uspto-grants-2013_01
Patent number
US08362012B2

Reaction notes

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