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

HRID 1962231Notes

Reaction equation

HRID 1962231 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

A heterogeneous mixture of 4-nitrophenol (5 g), methyl 2-bromoisobutyrate (5.6 mL) and K2CO3 (7.5 g) in acetone (60 mL) was refluxed overnight. The reaction mixture was then 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 (49).

Workup

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

Sources & evidence

ORD record
ord-e54ea624a5df4285a6c53488596a0e54
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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