Thioglycolic Acid → [{1-(6-Methyl-1,3-benzodioxol-5-yl)butyl}thio]acetic acid

HRID 486957Notes

Reaction equation

HRID 486957 reaction equation
[CH3:1][C:2]1[C:3]([CH:11](O)[CH2:12][CH2:13][CH3:14])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[SH:16][CH2:17][C:18]([OH:20])=[O:19].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C(OCC)(=O)C>C1C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH:11]([S:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:12][CH2:13][CH3:14])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 67784687(6-Methyl-1,3-benzodioxol-5-yl)butan-1-ol

Product 1

HCID 14514931[{1-(6-Methyl-1,3-benzodioxol-5-yl)butyl}thio]acetic acidYield 54%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5.6 g of (6-methyl-1,3-benzodioxol-5-yl)butan-1-ol, 4.8 g of mercaptoacetic acid and a catalytic amount of D-10-camphorsulfonic acid in 60 ml of benzene was heated under reflux for 3 hours, followed by the addition of ethyl acetate. The obtained mixture was washed with water and extracted with a 1N aqueous solution of sodium hydroxide. The aqueous layer was washed with ethyl acetate, acidified with 1N hydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent. The obtained residue was chromatographed over silica gel column and eluted with chloroform to obtain a colorless crystal. This crystal was recrystallized from isopropyl ether/hexane to obtain 4.1 g of the title compound as a colorless prismatic crystal.

Workup

  1. temperatureunder reflux for 3 hours
  2. washThe obtained mixture was washed with water
  3. extractionextracted with a 1N aqueous solution of sodium hydroxide
  4. washThe aqueous layer was washed with ethyl acetate
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe obtained residue was chromatographed over silica gel column
  10. washeluted with chloroform
  11. customto obtain a colorless crystal
  12. customThis crystal was recrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-5b8d38e398c44416a68e0328f122e65b
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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