Water → HCID 67512779, compound

HRID 244375Notes

Reaction equation

HRID 244375 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].O.C(O[CH2:27][CH3:28])(=O)C>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH3:15][C:4]1[CH:3]=[C:2]([O:1][CH2:16][CH:27]=[CH2:28])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58376048Methyl 4-hydroxy-2-Methyl-5-nitrobenzoate

Product 1

HCID 67512779HCID 67512779, compound

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-hydroxy-2-methyl-5-nitrobenzoate (6.3 g) in N,N-dimethyl-formamide (150 ml) were added at room temperature 18-crown-6 (79 mg) and potassium carbonate (8.3 g), and the mixture was stirred at 80° C. for one hour. The mixture was cooled to room temperature, and to the reaction solution were added water and ethyl acetate, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (7.5 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acb17f18e12e4257bed4406b09b9df21
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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