Chlorosulfonic acid → (2E)-3-[4-(Sulfooxy)phenyl]-2-propenoic acid

HRID 1604076Notes

Reaction equation

HRID 1604076 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH:6]1[C:11](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=[C:8]([OH:17])[CH:7]=1>N1C=CC=CC=1>[CH:6]1[C:11](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=[C:8]([O:17][S:2]([OH:5])(=[O:4])=[O:3])[CH:7]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid4×HCID 637542P-Coumaric Acid2×

Product 1

HCID 6070438(2E)-3-[4-(Sulfooxy)phenyl]-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid is added to the pyridine solution to form a reaction mixture. Preferably, the chlorosulfonic acid is added dropwise while maintaining the cooled temperature. About 1 mole of chlorosulfonic acid per mole of coumaric acid may be used. A slight excess is acceptable. Due to the reaction's exothermic nature, the reaction mixture is preferably stirred at the cooled temperature, e.g., about 0° C., for a time sufficient to allow the p-coumaric acid and the chlorosulfonic acid to react and form zosteric acid. Preferably, the reaction mixture is stirred for about 2 to about 4 hours at the low temperature, more preferably about 2.5 to about 3 hours.

Workup

  1. customto form a reaction mixture
  2. temperaturewhile maintaining the cooled temperature

Sources & evidence

ORD record
ord-24ea64d768cf442098c069f629b1af87
Source dataset
uspto-grants-1999_11
Patent number
US05990336

Reaction notes

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