HCID 232617, compound → 2-Methoxy-6-(2-nitrovinyl)phenyl acetate

HRID 596502Notes

Reaction equation

HRID 596502 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=[CH:10][N+:11]([O-:13])=[O:12])[C:4]=1[OH:14].[C:15]([O-])(=[O:17])[CH3:16].[Na+]>C(OC(=O)C)(=O)C.C(O)C>[C:15]([O:14][C:4]1[C:5]([CH:9]=[CH:10][N+:11]([O-:13])=[O:12])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 232617HCID 232617, compoundHCID 517045Sodium Acetate

Product 1

HCID 536784862-Methoxy-6-(2-nitrovinyl)phenyl acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 2-methoxy-6-(2-nitrovinyl)phenol (29.0 grams, 0.15 mole) and sodium acetate (12.4 grams, 0.15 mole) in acetic anhydride (100 ml.) was refluxed for 4 hours and then poured into ice water. The resulting semi-solid precipitate was dissolved in hot 95% ethanol. Cooling the solution precipitated the crude product which was purified for analysis by chromatography on silica gel with methylene chloride as elutant. The purified 2-methoxy-6-(2-nitrovinyl)phenyl acetate melted at 128° C.-129° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureCooling the solution
  3. customprecipitated the crude product which
  4. customwas purified for analysis by chromatography on silica gel with methylene chloride as elutant

Sources & evidence

ORD record
ord-7bc0b51a4c9847f4a35dbc7a8db02a92
Source dataset
uspto-grants-1977_03
Patent number
US04011230

Reaction notes

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