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

HRID 486895Notes

Reaction equation

HRID 486895 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 and the mixture was heated under reflux for 4 h. The solvent was distilled off and the pH of the residue was adjusted to 10 with 1N aqueous sodium hydroxide solution. After washing with ethyl acetate, 4N hydrochloric acid was added thereto under cooling with ice to acidify the aqueous layer. After extraction with chloroform, the extract was washed with water and dried over anhydrous magnesium sulfate. It was filtered and the filtrate was concentrated. The crystals thus formed were recrystallized from diisopropyl ether to obtain 62.70 g of the intended compound in the form of colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 h
  3. distillationThe solvent was distilled off
  4. washAfter washing with ethyl acetate, 4N hydrochloric acid
  5. additionwas added
  6. temperatureunder cooling with ice
  7. extractionAfter extraction with chloroform
  8. washthe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationIt was filtered
  11. concentrationthe filtrate was concentrated
  12. customThe crystals thus formed
  13. customwere recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b4e04dae3d364c879e13080143fdc58d
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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