Sulfuric Acid → HCID 20026748, compound

HRID 1723170Notes

Reaction equation

HRID 1723170 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1.C(N(CC)CC)C.S(=O)(=O)(O)O>O1CCOCC1>[C:3]([CH2:2][S:1][CH:11]([C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:17][CH:16]=1)[CH2:12][C:13]([OH:15])=[O:14])([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-

Product 1

HCID 20026748HCID 20026748, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred mixture of mercaptoacetic acid (5.04 g, 3.8 ml, 54.7 mmol) and 4-chlorocinnamic acid (10.0 g, 54.7 mmol) in 20 ml of dioxane is added dropwise a solution of triethylamine (6.90 g, 9.53 ml, 68.0 mmol) in 20 ml of dioxane. The mixture is heated under reflux for 5 hours, then cooled and poured into ice, acidified with conc. sulfuric acid and extracted with ether. The combined ether extracts are washed with water and with brine, dried and stripped of the solvent. The residue is washed with chloroform to give 3-carboxymethylthio-3-(4-chlorophenyl)propionic acid, a yellow solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. additionpoured into ice
  5. extractionextracted with ether
  6. washThe combined ether extracts are washed with water and with brine
  7. customdried
  8. washThe residue is washed with chloroform

Sources & evidence

ORD record
ord-b9c84c5e32994f1e8529c65a99c55fcc
Source dataset
uspto-grants-1989_08
Patent number
US04859699

Reaction notes

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