Thioglycolic Acid → 2-(phenethylthio)acetic acid

HRID 1027899Notes

Reaction equation

HRID 1027899 reaction equation
[OH-].[Na+].[SH:3][CH2:4][C:5]([OH:7])=[O:6].Cl[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[CH2:9]([S:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 2314961-Chloro-2-phenylethane

Product 1

HCID 2925402-(phenethylthio)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1 L flask, solid sodium hydroxide (10.50 g, 0.263 mol) was dissolved in MeOH (150 ml), and then slowly combined with 2-mercaptoacetic acid (11.51 g, 0.125 mol). The mixture was then treated in portions with (2-chloroethyl)benzene (19.33 g, 0.138 mol), heated at reflux for 10 hours, stirred for 6 hours at ambient temperature, concentrated to dryness on a rotovap, treated with water (500 mL) and extracted with Et2O (2×150 mL). These Et2O extractions were discarded. The aqueous layer was acidified to pH ˜2 with concentrated HCl and extracted with Et2O (2×150 mL). These Et2O extractions were combined, washed with brine, dried (MgSO4), filtered and concentrated to provide the title compound. 1H NMR (CDCl3) δ 2.93 (s, 4H), 3.25 (s, 2H), 7.17-7.34 (m, 5H); MS (M+NH4)+ m/z 214.

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 hours
  3. concentrationconcentrated to dryness on a rotovap
  4. additiontreated with water (500 mL)
  5. extractionextracted with Et2O (2×150 mL)
  6. extractionThese Et2O extractions
  7. extractionextracted with Et2O (2×150 mL)
  8. extractionThese Et2O extractions
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-4b8cd76e3bec4512a8e35b33905fb4fd
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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