Lithium hydroxide, monohydrate → Propionic acid, 2-methyl-2-(phenylthio)-

HRID 2247309Notes

Reaction equation

HRID 2247309 reaction equation
[CH3:1][C:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:7])[C:3]([O:5]C)=[O:4].O.[OH-].[Li+]>C1COCC1.CO>[CH3:7][C:2]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12467092HCID 12467092, compound

Product 1

HCID 199886Propionic acid, 2-methyl-2-(phenylthio)-Yield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-methyl-2-(phenylthio)propanoate (1.126 g, 5.35 mmol) was dissolved in THF (15 mL) and methanol (5 mL). That solution was treated with an aqueous solution of lithium hydroxide monohydrate (1.12 g, 26.8 mmol in 5 mL of water). The reaction mixture was stirred at rt overnight. The volatiles were removed and the remaining aqueous solution was acidified with a 1 N HCl solution to pH 2. Ethyl acetate was added and the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated to provide the desired carboxylic acid as a white solid (1.020 g, 97.1% yield).

Workup

  1. customThe volatiles were removed
  2. additionEthyl acetate was added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-195f2a2668a4448cb9e844135f57c42f
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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