Water → Tert-butyl 2-(4-nitrophenoxy)acetate

HRID 1802045Notes

Reaction equation

HRID 1802045 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].O>CN(C=O)C.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22061043Tert-butyl 2-(4-nitrophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitrophenol (3.00 g, 21.6 mmol) and K2CO3 (6.00 g, 43.4 mmol) in DMF (50 mL), t-butyl bromoacetate (2.90 mL, 19.6 mmol) was added. The mixture was stirred at room temperature for 5 h. Water and EtOAc were added. The organic phase was separated, washed with water, then with aq. 1N NaOH and brine. It was dried over Na2SO4, concentrated in vacuo to give tert-butyl 2-(4-nitrophenoxy)acetate as a solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialIt was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27cde78197634f539d07f0eb5fb757da
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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