Hydrochloric Acid → 3-Nitro-5-vinylbenzoic acid methyl ester

HRID 1280136Notes

Reaction equation

HRID 1280136 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][Si](C)(C)C)[CH:7]=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1.Cl>C(#N)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[CH:7]=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543670333-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

Product 1

HCID 540267313-Nitro-5-vinylbenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester (2.44 g, 8.71 mmol) was dissolved in acetonitrile (150 ml), the solution was heated to reflux temperature and HCl gas was bubbled through the solution until the starting material had disappeared according to HPLC analysis. The solution was allowed to cool and the solvent was removed by evaporation. The residue was >95% pure according to HPLC and was used without further purification. Yield: 2.02 g (89%).

Workup

  1. temperaturethe solution was heated
  2. customwas bubbled through the solution until the starting material
  3. temperatureto cool
  4. customthe solvent was removed by evaporation
  5. customwas used without further purification

Sources & evidence

ORD record
ord-92393717dcd344efbd6f9f5af65429a9
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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