Sodium Hydroxide → Ethyl 3-mercapto-2-methylpropanoate

HRID 258476Notes

Reaction equation

HRID 258476 reaction equation
[OH-].[Na+].C([S:6][CH2:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)C>CO>[SH:6][CH2:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15289598Ethyl 3-(acetylsulfanyl)-2-methylpropanoate

Product 1

HCID 15289599Ethyl 3-mercapto-2-methylpropanoateYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At -20° C., 3N NaOH (150 mL, 450 mmol) was added dropwise to a solution of ethyl 3-(acetylthio)-2-methylpropanoate (66.47 g, 349 mmol, obtained from ethyl methacrylate as in Example 10, Step 1) in 700 mL of MeOH and the mixture was stirred at that temperature for 30 min. 25% Aq NH4OAc was then added and the title thiol was extracted with EtOAc, dried over MgSO4, concentrated and distilled to yield 42.52 g (82%) of the title compound as an oil; bp: 96°-98° C./15 mm Hg.

Workup

  1. extractionthe title thiol was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-0fca54130d974c038ee9154589be4d22
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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