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

HRID 2395985Notes

Reaction equation

HRID 2395985 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 temperaturefor 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 pH1 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 pH1 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-9d70bcebcb2847dfaec7658445293f50
Source dataset
uspto-grants-1996_02
Patent number
US05491142

Reaction notes

Loading…