4-Nitrophenol → Methyl 2-methyl-2-(4-nitrophenoxy)propanoate

HRID 1962255Notes

Reaction equation

HRID 1962255 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 90097Methyl 2-bromo-2-methylpropionate

Product 1

HCID 57562956Methyl 2-methyl-2-(4-nitrophenoxy)propanoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Nitrophenol (5 g), methyl 2-bromoisobutyrate (5.6 mL) and K2CO3 (7.5 g) were suspended in acetone (60 mL). The yellow solution was refluxed overnight. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were evaporated to give methyl 2-(4-nitrophenoxy)isobutyrate.

Workup

  1. temperatureThe yellow solution was refluxed overnight
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-4b90398768654532a9b68b69a7eae6ed
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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