Hydrochloric Acid → Methyl [4-(2-nitrovinyl)phenyl]sulphone

HRID 586625Notes

Reaction equation

HRID 586625 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N+:13]([CH3:16])([O-:15])=[O:14].[OH-].[Na+].Cl>CO>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:16][N+:13]([O-:15])=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 69794186Methyl [4-(2-nitrovinyl)phenyl]sulphone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
3 °C

Procedure

A mixture of 4-methylsulphonylbenzaldehyde (22.08 g, 120 mmol) and nitromethane (12.5 ml, 14.2 g, 233 mmol) in MeOH (1 l) is cooled to 3° C. in an ice bath; sodium hydroxide solution (32%, 420 ml, 567 g, 135 g of NaOH, 3.36 mol) is then added dropwise, a clear solution being formed after addition of 30 ml (time needed 1 h). The mixture is stirred at 10° C. for 2 h and then added dropwise at 10° C. to initially introduce HCl (20%, 1080 ml, 216 g of HCl, 5.9 mol) (time needed 40 min). The HCl-acidic mixture is stirred until formation of the precipitate is complete (30 min). The nitrostyrene crystallizate is filtered off with suction, washed with ice water until the wash phase gives a neutral reaction and dried over P2O5 in an evacuated desiccator. The yield of crystallizate is 16.03 g after drying.

Workup

  1. customa clear solution being formed
  2. additionafter addition of 30 ml (time needed 1 h)
  3. custom(30 min)
  4. filtrationThe nitrostyrene crystallizate is filtered off with suction
  5. washwashed with ice water until the wash phase
  6. customgives
  7. customa neutral reaction
  8. dry with materialdried over P2O5 in an evacuated desiccator
  9. customafter drying

Sources & evidence

ORD record
ord-de8aa1a83796439e9d39071e93a21761
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

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