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

HRID 1195310Notes

Reaction equation

HRID 1195310 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[CH3:21][C:22]1[C:23]([CH:31](O)[CH3:32])=[CH:24][C:25]2[O:29][CH2:28][O:27][C:26]=2[CH:30]=1>C1C=CC=CC=1>[CH3:21][C:22]1[C:23]([CH:31]([S:1][CH2:2][C:3]([OH:5])=[O:4])[CH3:32])=[CH:24][C:25]2[O:29][CH2:28][O:27][C:26]=2[CH:30]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 145148961-(6-Methyl-1,3-benzodioxol-5-yl)ethanol

Product 1

HCID 14514909[{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}thio]acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.7 g of mercaptoacetic acid and a catalytic amount of D-10-camphorsulfonic acid were added to 3.2 g of 1-(6-methyl-1,3-benzodioxol-5-yl)ethanol, followed by the addition of 100 ml of benzene. The obtained mixture was heated under reflux for one hour, washed with water and extracted with a 1N aqueous solution of sodium hydroxide. The aqueous layer was washed with ethyl acetate, acidified with 1 N hydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent. The obtained crystalline residue was recrystallized from diisopropyl ether to obtain 4.2 g of the title compound as a colorless crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for one hour
  3. washwashed with water
  4. extractionextracted with a 1N aqueous solution of sodium hydroxide
  5. washThe aqueous layer was washed with ethyl acetate
  6. extractionextracted with chloroform
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe obtained crystalline residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b992a523cc424bdea0153ee848ef90ed
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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