Ethanol → HCID 22053927, compound

HRID 1830117Notes

Reaction equation

HRID 1830117 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([CH2:15][S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.O.O1CCOCC1.C(O)C>[OH-].[K+]>[CH2:8]([S:7][CH2:6][CH:5]([CH2:15][S:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:4]([OH:24])=[O:3])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 312751,4-DioxaneHCID 69437475HCID 69437475, compound

Product 1

HCID 22053927HCID 22053927, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

3-Benzylsulfanyl-2-benzylsulfanylmethyl-propionic acid ethyl ester (1.589 g, 4.41 mmol) in a mixture of potassium hydroxide (1N, 7 mL), water (3 mL), dioxane (30 mL) and ethanol (10 mL) was stirred at room temperature for 18 hours. The solvents were removed form the reaction mixture by rotary evaporation at reduced pressure and the residue was dissolved in water and washed with ether. The aqueous layer was cooled on ice, acidified to pH 2 and the product extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure to give 3-benzylsulfanyl-2-benzylsulfanylmethyl-propionic acid (1.293 g, 88%).

Workup

  1. customThe solvents were removed form the reaction mixture
  2. customby rotary evaporation at reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washwashed with ether
  5. temperatureThe aqueous layer was cooled on ice
  6. extractionthe product extracted with ethyl acetate
  7. washThe extracts were washed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed by rotary evaporation at reduced pressure

Sources & evidence

ORD record
ord-7985cc0dff144165bfe68e27f60779ed
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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