Sodium Hydroxide → HCID 14514913, compound

HRID 2259782Notes

Reaction equation

HRID 2259782 reaction equation
[CH2:1]([C:3]1[C:4]([CH:12]([S:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH2:13][CH3:14])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1)[CH3:2].[OH-].[Na+]>O.C(O)C>[CH2:1]([C:3]1[C:4]([CH:12]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH3:14])=[CH:5][C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54155954HCID 54155954, compound

Product 1

HCID 14514913HCID 14514913, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.0 g of ethyl [{1-(6-ethyl-1,3-benzodioxol-5-yl)-propyl}thio]acetate and 2.6 g of sodium hydroxide were dissolved in a mixture comprising 20 ml of water and 20 ml of ethanol. The obtained solution was heated under reflux for 2 hours and distilled to remove the ethanol. The residue was washed with ether. The aqueous layer was acidified and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.8 g of the title compounds as a colorless crystal.

Workup

  1. temperatureThe obtained solution was heated
  2. temperatureunder reflux for 2 hours
  3. distillationdistilled
  4. customto remove the ethanol
  5. washThe residue was washed with ether
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in a vacuum
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8)

Sources & evidence

ORD record
ord-e0750123b49046cc87189ec50660d6ef
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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