Sodium Hydroxide → HCID 14514913, compound

HRID 2259736Notes

Reaction equation

HRID 2259736 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)-1-propyl}thio]acetate and 2.6 g of sodium hydroxide were dissolved in a mixture of 20 ml of water and 20 ml of ethanol. The solution was heated under reflux for 2 h. Ethanol was distilled off and 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 under reduced pressure. The residue was purified according to silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.8 g of the intended compound in the form of white crystals.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 h
  3. distillationEthanol was distilled off
  4. washthe residue was washed with ether
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified

Sources & evidence

ORD record
ord-62b8667d25f64f6c9bc87af352b5999c
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

Loading…