Acetic Acid → HCID 86073592, compound

HRID 1350785Notes

Reaction equation

HRID 1350785 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12](O)=[O:13])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18](O)(=O)C.[CH3:22][OH:23]>CC#N>[CH3:22][O:23][C:12](=[O:13])[CH2:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([O:1][CH3:18])=[C:3]([N+:15]([O-:17])=[O:16])[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 985963,5-Dinitro-4-hydroxyphenacetic acid

Product 1

HCID 86073592HCID 86073592, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of TMSCHCN2 (1.0 M) was added to 4.28 g (17.3 mmol) of (4-hydroxy-3,5-dinitro-phenyl)-acetic acid in 63 mL of MeCN and 7 mL of MeOH. After 2 h, 0.8 mL of acetic acid was added. After stirring an additional 30 min, the solution was concentrated and partitioned between saturated NaHCO3 and EtOAc. The organic portion was washed with brine, dried with Na2SO4, filtered, and concentrated to provide (4-methoxy-3,5-dinitro-phenyl)-acetic acid methyl ester (3.22 g).

Workup

  1. concentrationthe solution was concentrated
  2. custompartitioned between saturated NaHCO3 and EtOAc
  3. washThe organic portion was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ed6e80ae81f426b9f205e0d48c58984
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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