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

HRID 486953Notes

Reaction equation

HRID 486953 reaction equation
Cl[CH2:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[SH:13][CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>C(O)C>[CH3:12][C:11]1[C:3]([CH2:2][S:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 105594165-(Chloromethyl)-6-methylbenzo[d][1,3]dioxole

Product 1

HCID 14514915[{(6-Methyl-1,3-benzodioxol-5-yl)methyl}thio]acetic acidYield 20.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6.0 g of 5-chloromethyl-6-methyl-1,3-benzodioxole, 6.0 g of mercaptoacetic acid and 6.5 g of sodium hydroxide in 130 ml of 50% aqueous ethanol was heated under reflux for one hour and concentrated, followed by the addition of water. The mixture was washed with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid and extracted with chloroform. The organic layer was dried over magnesium sulfate and distilled to remove the solvent. The residue was chromatographed over a silica gel column and eluted with chloroform to obtain a crude crystal. This crude crystal was recrystallized from diisopropyl ether to obtain 1.6 g of the title compound as a colorless crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. concentrationconcentrated
  4. additionfollowed by the addition of water
  5. washThe mixture 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 residue was chromatographed over a silica gel column
  11. washeluted with chloroform
  12. customto obtain a crude crystal
  13. customThis crude crystal was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0aa97f3bad604b8cb28a466dcb9d34c7
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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