Thioglycolic Acid → [{2-(1,3-Benzodioxol-5-yl)-2-propyl}thio]acetic acid

HRID 1195309Notes

Reaction equation

HRID 1195309 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:30](O)([CH3:32])[CH3:31])=[CH:29][C:24]=2[O:23][CH2:22]1>C1C=CC=CC=1>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:30]([S:1][CH2:2][C:3]([OH:5])=[O:4])([CH3:32])[CH3:31])=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 118196322-(Benzo[d][1,3]dioxol-5-yl)propan-2-ol

Product 1

HCID 14514907[{2-(1,3-Benzodioxol-5-yl)-2-propyl}thio]acetic acidYield 45.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

600 ml of benzene, 59.5 g of mercaptoacetic acid and a catalytic amount of D-10-camphorsulfonic acid were added to 97 g of 2-(1,3-benzodioxol-5-yl)-2-propanol. The obtained mixture was heated under reflux for 4 hours and distilled to remove the solvent. The pH of the residue was adjusted to 10 with a 1N aqueous solution of sodium hydroxide. The resulting mixture was washed with ethyl acetate. 4N hydrochloric acid was added to the mixture under cooling with ice to acidify the aqueous layer. The resulting mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to obtain a crude crystal. This crude crystal was recrystallized from diisopropyl ether to obtain 62.70 g of the title compound as a colorless crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 4 hours
  3. distillationdistilled
  4. customto remove the solvent
  5. washThe resulting mixture was washed with ethyl acetate
  6. addition4N hydrochloric acid was added to the mixture
  7. temperatureunder cooling with ice
  8. extractionThe resulting mixture was extracted with chloroform
  9. washThe organic layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated
  13. customto obtain a crude crystal
  14. customThis crude crystal was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-54e507e52c7f404aaf8860f0bbfdf2b5
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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