Thioglycolic Acid → HCID 13393822, compound

HRID 978786Notes

Reaction equation

HRID 978786 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].[C:20]([OH:24])(=[O:23])[CH2:21][SH:22].C(=O)(O)[O-].[Na+]>C(O)C>[C:20]([CH2:21][S:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19])([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 516892Sodium BicarbonateHCID 13393783HCID 13393783, compound

Product 1

HCID 13393822HCID 13393822, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 2.7 g 4-chloro-3-formyl-flav-3-ene, 0.85 ml thioglycolic acid and 2.5 g sodium bicarbonate in 30 ml absolute ethanol is refluxed for 15 hours. After evaporation, one adds water and extracts with methylene chloride. The aqueous phase is acidified to pH 1. Extraction with methylene chloride is followed by washing the organic solution with water, drying over magnesium sulfate and evaporation. The residue is purified by column chromatography on silicagel using a mixture of methylene chloride and ethanol as eluant. The best fractions are crystallized in a mixture of hexane and toluene. Pure 4-(S-carboxymethylthio)-3-formyl-flav-3-ene is obtained as yellow crystals; m.p. 127°-129° C.

Workup

  1. temperatureis refluxed for 15 hours
  2. customAfter evaporation, one
  3. additionadds water and extracts with methylene chloride
  4. extractionExtraction with methylene chloride
  5. washby washing the organic solution with water
  6. dry with materialdrying over magnesium sulfate and evaporation
  7. customThe residue is purified by column chromatography on silicagel
  8. additiona mixture of methylene chloride and ethanol as eluant
  9. customThe best fractions are crystallized in a mixture of hexane and toluene

Sources & evidence

ORD record
ord-1e055fc995d9464283153ff044db1c1f
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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