Sodium Hydroxide → Ethyl 3-mercapto-2-methylpropanoate

HRID 341981Notes

Reaction equation

HRID 341981 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, Step 5) in 700 mL of MeOH and the mixture was stirred at that temperature for 30 min. 25% Ag 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-2426009d1e2940a89a3c3201124978ad
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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