Water → t-Butyl 3-methyl-4-nitrophenoxyacetate

HRID 1592027Notes

Reaction equation

HRID 1592027 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 23370041t-Butyl 3-methyl-4-nitrophenoxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.53 g (10 mmol) of 3-methyl-4-nitrophenol, 1.95 g (10 mmol) of t-butyl bromoacetate and 2.76 g (20 mmol) of potassium carbonate in 10 mL of DMF are stirred at RT for 2 h. Water is added and the mixture is extracted with EtOAc and the organic phase is washed with water and brine, and dried over anhydrous Na2SO4. The solvent is removed under reduced pressure and the residual oil is filtered through a pad of silica gel using CH2Cl2 as the eluant to give (3-methyl-4-nitrophenoxy)-acetic acid t-butyl ester as an oil: 1H-NMR (CDCl3) δ 8.08 (d, J=9.56, 1H), 6.82-6.75 (m, 2H), 4.58 (s, 2H), 2.63 (s, 3H), 1.49 (s, 9H); Anal. Calcd for C13H17NO5 C, 58.42; H, 6.41; N, 5.24; Found C, 58.04; H, 6.51; N, 5.09.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washthe organic phase is washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent is removed under reduced pressure
  5. filtrationthe residual oil is filtered through a pad of silica gel

Sources & evidence

ORD record
ord-7a24676ed10642cab6c35de48e9600ae
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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