Sodium Hydroxide → (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)methylene]succinic acid

HRID 1740833Notes

Reaction equation

HRID 1740833 reaction equation
C([O:3][C:4](/[C:6](=[C:11](\[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)/[CH2:7][C:8]([OH:10])=[O:9])=[O:5])C.[OH-].[Na+]>C(O)C.O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22](/[C:11](=[C:6](/[CH2:7][C:8]([OH:10])=[O:9])\[C:4]([OH:5])=[O:3])/[C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:16][CH:17]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11048119HCID 11048119, compound

Product 1

HCID 21833695(Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)methylene]succinic acidYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 50 g (0.118 mole) of (Z)-3-ethoxycarbonyl-4-(4-chlorophenyl)-4-(4-methanesulphonylphenyl)-3-butenoic acid, prepared in example 3, in 1000 ml of ethanol is added a solution of 10.4 g (0.26 mole) of sodium hydroxide in 25 ml of water. The mixture is heated under reflux for 6 hours, the precipitate is filtered off and washed with ethanol. The solid is then taken up into 500 ml of a 1N sodium hydroxide solution and the insoluble is filtered off. The aqueous phase is washed with dichloromethane and then acidified with hydrochloric acid to pH=1. After one hour's stirring, the precipitate obtained is filtered under suction, washed with water and dried to give 38.4 g of (Z)-2-[1-(4-chlorophenyl)-1-(4-methanesulphonylphenyl)-methylene]succinic acid in the form of crystals with a melting point of 199-200° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe precipitate is filtered off
  4. washwashed with ethanol
  5. filtrationthe insoluble is filtered off
  6. washThe aqueous phase is washed with dichloromethane
  7. customthe precipitate obtained
  8. filtrationis filtered under suction
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-72a469e80fff4f75b17ee7311a8f9278
Source dataset
uspto-grants-1999_10
Patent number
US05972950

Reaction notes

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