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

HRID 486899Notes

Reaction equation

HRID 486899 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(Cl)(Cl)Cl>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

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 6212ChloroformHCID 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% hydrous ethanol was heated under reflux for 1 h. The reaction mixture was concentrated. Water was added thereto and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 1Nhydrochloric acid. After extraction with chloroform, the extract was dried over magnesium sulfate. The solvent was distilled off and the product was isolated according to silica gel column chromatography (chloroform). The crystals thus obtained were recrystallized from diisopropyl ether to obtain 1.6 g of the intended compound in the form of white crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. additionWater was added
  5. washthe mixture was washed with ethyl acetate
  6. extractionAfter extraction with chloroform
  7. dry with materialthe extract was dried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe product was isolated
  10. customThe crystals thus obtained
  11. customwere recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2cdbc011d78d4871827a72c28ac197c6
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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