Water → Propanoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-2-methyl-

HRID 22515Notes

Reaction equation

HRID 22515 reaction equation
[C:1]([C:6]([S:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)([CH3:8])[CH3:7])([O:3]CC)=[O:2].O.O1CCCC1.[OH-].[K+]>C(O)C>[C:1]([C:6]([S:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)([CH3:7])[CH3:8])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 19974022HCID 19974022, compound

Product 1

HCID 10421773Propanoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-2-methyl-Yield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2-(carboethoxy)-2-(4-methoxybenzylthio)propane (1.05 g, 3.91 mmol) in a mixture of 95% ethanol (18 mL), water (9 mL) and tetrahydrofuran (10 mL). Add potassium hydroxide (1.4 g, 25 mmol) and stir at room temperature for 2 hours then at 55° C. for 1 hour. Evaporate the solvent in vacuo and partition between water (50 mL) and ether (50 mL). Acidify to pH 1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 2-(carboxy)-2-(4-methoxybenzylthio)propane as a tan solid (763 mg).

Workup

  1. customEvaporate the solvent in vacuo
  2. custompartition between water (50 mL) and ether (50 mL)
  3. extractionAcidify to pH 1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL)
  4. dry with materialDry (Na2SO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-01d2ae62f6df4e2da6d5676db9a9d861
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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