Water → HCID 67513029, compound

HRID 244373Notes

Reaction equation

HRID 244373 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(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([O: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:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58376048Methyl 4-hydroxy-2-Methyl-5-nitrobenzoate

Product 1

HCID 67513029HCID 67513029, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-hydroxy-2-methyl-5-nitrobenzoate (12.9 g) was dissolved in dimethylformamide (200 ml), and thereto were added potassium carbonate (20.1 g) and benzyl bromide (13.7 g), and the mixture was stirred at 70° C. for 4 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The obtained organic layer was washed with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained solid was washed with hexane/ethyl acetate=10/1 to give the title compound (13 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. washThe obtained solid was washed with hexane/ethyl acetate=10/1

Sources & evidence

ORD record
ord-2b032d51f2834a6fa2c8a3826b2acfad
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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