Acetic Acid → HCID 86073592, compound

HRID 2109290Notes

Reaction equation

HRID 2109290 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-8eef1690e7604b0c9cfd4fe121b43c1d
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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