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

HRID 2259733Notes

Reaction equation

HRID 2259733 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 and the mixture was heated under reflux in 100 ml of benzene for 1 h. The reaction mixture was washed with water and then extracted with a 1 1N sodium hydroxide solution. 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 the solvent was distilled off to obtain a crystalline residue. After recrystallization from diisopropyl ether, 4.2 g of the intended compound was obtained in the form of white crystals.

Workup

  1. temperaturethe mixture was heated
  2. washThe reaction mixture was washed with water
  3. extractionextracted with a 1 1N sodium hydroxide solution
  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. distillationthe solvent was distilled off
  8. customto obtain a crystalline residue
  9. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-122a77979096458d99b4008e72393cdb
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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