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

HRID 1725701Notes

Reaction equation

HRID 1725701 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-dfcdd087fe1644e99869c51569e9f4fd
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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