Dimethyl 2,2'-(ethane-1,2-diyldisulfanediyl)diacetate → (Ethylenedithio)diacetic Acid

HRID 874056Notes

Reaction equation

HRID 874056 reaction equation
[CH2:1]([S:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:2][S:3][CH2:4][C:5]([O:7]C)=[O:6]>Cl>[CH2:2]([S:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:1][S:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 20386761Dimethyl 2,2'-(ethane-1,2-diyldisulfanediyl)diacetate

Product 1

HCID 310815(Ethylenedithio)diacetic Acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl 2,2′-(ethane-1,2-diylbis(sulfanediyl))diacetate (7.00 g, 29.4 mmol) was heated to reflux for two hours in 2 N HCl (50 mL). Cooling the mixture to room temperature gave a clear solution, which was concentrated to dryness in vacuo, giving Compound 3 as a white solid, 5.98 g (96.8%). 1H NMR (400 MHz, D2O) δ 3.47 (s, 4H), 2.95 (s, 4H). 13C NMR (101 MHz, D2O) δ 174.61, 33.28, 31.39.

Workup

  1. customgave a clear solution, which
  2. concentrationwas concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-dc446f222bd04a77bbda9348004a3cc6
Source dataset
uspto-grants-2015_03
Patent number
US08980077B2

Reaction notes

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