Thioglycolic Acid → [(4-nitrobenzyl)thio]acetic acid

HRID 1081376Notes

Reaction equation

HRID 1081376 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[SH:12][CH2:13][C:14]([OH:16])=[O:15]>[OH-].[Na+].C1COCC1.O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 1133Thioglycolic AcidHCID 74824-Nitrobenzyl chloride

Product 1

HCID 242647[(4-nitrobenzyl)thio]acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

4-Nitrobenzyl chloride (2.5 g, 15 mmol) was added to a solution of mercaptoacetic acid (80% in H2O, 1 mL,~12 mmol) in aqueous sodium hydroxide (2.75N, 10 mL) and THF (10 mL) with stirring at 50° C. After 1 hour, the reaction was cooled to ambient temperature, diluted with water (30 mL) and extracted with Et2O to remove excess halide. The aqueous layer was distributed between EtOAc and 5% citric acid and the organic extract then washed with H2O, dried (MgSO4) and evaporated to give the title compound as a pale yellow solid, m.p. 101-104° C. [lit. m.p. 114° C⟧ 1H NMR (CDCl3); δ3.10 (s, 2H), 3.94 (s, 2H), 5.37 (d, 2H, J =8.7 Hz), 8.21 (d, 2H, J=8.7 Hz).

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. extractionextracted with Et2O
  3. customto remove excess halide
  4. extractionthe organic extract
  5. washthen washed with H2O
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-48d1dacdc98f4016b553cbd60b6604f6
Source dataset
uspto-grants-1996_12
Patent number
US05585359

Reaction notes

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