3-Nitrophenol → Ethyl 2-methyl-2-(3-nitrophenoxy)propanoate

HRID 1487146Notes

Reaction equation

HRID 1487146 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:18][C:12]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 22060504Ethyl 2-methyl-2-(3-nitrophenoxy)propanoateYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitrophenol (7.5 g, 53.9 mmol) and ethyl 2-bromo-2-methylpropanoate (12.62 g, 64.7 mmol) in DMF (25 ml) was added K2CO3 (14.90 g, 108 mmol). After stirring at rt for 16 hr, the reaction mixture was concentrated under vacuum. The residue was diluted with water and extracted with ethyl acetate (3×30 ml), the combined organic layer was washed with NaOH solution (10%, 75 mL), water (75 mL) and brine, dried over sodium sulphate and concentrated under vacuum to give the title product (6.7 g).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washthe combined organic layer was washed with NaOH solution (10%, 75 mL), water (75 mL) and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4ed6a789e02c43d99852ad008086bffe
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

Loading…