Maleic Anhydride → 3-(2-Chloro-5-nitrophenylsulphonyl)-propionic acid

HRID 978632Notes

Reaction equation

HRID 978632 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:13])=[O:12].[Na+].C(=O)([O-])O.[Na+].C1(=O)[O:25][C:23](=[O:24])[CH:22]=[CH:21]1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 7923Maleic Anhydride2×HCID 111522Benzenesulfinic acid, 2-chloro-5-nitro-, sodium salt (1:1)HCID 516892Sodium Bicarbonate2×

Product 1

HCID 137502573-(2-Chloro-5-nitrophenylsulphonyl)-propionic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

36 g of sodium 2-chloro-5-nitrobenzenesulphinate, 12.6 g of solid sodium hydrogen carbonate and 22.5 g of maleic anhydride are heated at 100° C. in 250 ml of water for 3 hours. After cooling down, a further 12.6 g of sodium hydrogencarbonate and 22.5 g of maleic anhydride are then added. After a further 5 hours of stirring at 100° C., the cooled, weakly acid reaction mixture is filtered with suction. The filter is cake at 50° C. in 300 ml of water, and the suspension is cooled down to 20° C. and is filtered again with suction. Drying gives 35.1 g of 3-(2-chloro-5-nitrophenylsulphonyl)-propionic acid.

Workup

  1. temperatureAfter cooling down
  2. customthe cooled, weakly acid reaction mixture
  3. filtrationis filtered with suction
  4. customat 50° C.
  5. temperaturethe suspension is cooled down to 20° C.
  6. filtrationis filtered again with suction
  7. customDrying

Sources & evidence

ORD record
ord-9ec27545afc14c46827e073c8719b23b
Source dataset
uspto-grants-1987_05
Patent number
US04665179

Reaction notes

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