Thionyl Chloride → 3-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

HRID 1013057Notes

Reaction equation

HRID 1013057 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13](O)(=[O:15])=[O:14])[CH:8]=1.S(Cl)([Cl:20])=O>CN(C)C=O>[CH3:2][O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([Cl:20])(=[O:15])=[O:14])[CH:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 725282343-(3-Sulfophenyl)acrylic acid methyl ester

Product 1

HCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To the sodium salt of 3-(3-sulfophenyl)acrylic acid methyl ester (2) (0.670 g, 2.53 mmol) benzene (2 mL), thionyl chloride (1.508 g, 0.9 mL, 12.67 mmol) and 3 drops of dimethylformamide were added and the resultant suspension was stirred at reflux for one hour. The reaction mixture was evaporated, the residue was dissolved in benzene (3 mL), filtered and the filtrate was evaporated to give the title compound (0.640 g, 97%).

Workup

  1. temperatureat reflux for one hour
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in benzene (3 mL)
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-535a27dcd1b843cea4eb1bb4d361a6ed
Source dataset
uspto-grants-2011_07
Patent number
US07981895B2

Reaction notes

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