Diethyl Ether → Methyl 2-methoxy-3-nitrobenzoate

HRID 618242Notes

Reaction equation

HRID 618242 reaction equation
O[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7]C=1C(O)=O.IC.[C:16](=[O:19])([O-])[O-].[K+].[K+].C[CH2:23][O:24][CH2:25][CH3:26].CN(C)C=[O:30]>>[CH3:23][O:24][C:25](=[O:30])[C:26]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[O:19][CH3:16]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 68073-Nitrosalicylic acidHCID 11430Potassium Carbonate

Product 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate

Conditions

Temperature
45 °C

Procedure

A solution of 15 g of 2-hydroxy-3-nitro-benzoic acid in 200 ml of N,N-dimethylformamide was treated with 58.1 g of iodomethane and 56.6 g of potassium carbonate, and the resultant heterogeneous mixture was stirred and heated to 45° C. for 20 hr. The mixture was cooled to room temperature, poured into ether, washed with water, washed with saturated sodium carbonate solution, washed with water, dried over magnesium sulfate, evaporated, and 14.2 g of 2-methoxy-3-nitro-benzoic acid methyl ester obtained as an oil which crystallized to a white solid. ##STR135##

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. washwashed with saturated sodium carbonate solution
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ba6db051f99e446099d47640d714d522
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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