Sodium Hydroxide → Ethyl 3-mercapto-2-methylpropanoate

HRID 22425Notes

Reaction equation

HRID 22425 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-(acetyl-thio)-2-methylpropanoate (66.47 g, 349 mmol, 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 mmHg. 1H NMR (CDC13): δ1.21-1.36 (6H, m), 1.50 (1H, t, SH), 2.66 (2H, m), 2.81 (1H, m), 4.19 (2H, q).

Workup

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

Sources & evidence

ORD record
ord-81a7c11200bf44f0955c35f62a9321da
Source dataset
uspto-grants-1995_06
Patent number
US05428033

Reaction notes

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