Hydrochloric Acid → HCID 19956284, compound

HRID 1779497Notes

Reaction equation

HRID 1779497 reaction equation
[O:1]=[C:2]([C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28]CC)=[O:27])=[CH:22][CH:21]=1)[CH2:3][S:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1.[OH-].[Na+].Cl>C(O)C>[C:16]([C:7]1[CH:6]=[C:5]([S:4][CH2:3][C:2]([C:20]2[CH:21]=[CH:22][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([OH:28])=[O:27])=[CH:33][CH:34]=2)=[O:1])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]=1[OH:15])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19956261HCID 19956261, compound

Product 1

HCID 19956284HCID 19956284, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.86 g (0.01 mol) of ethyl 2-{4-[1-oxo-2-(4-hydroxy-3,5-di-tert-butylphenylthio)ethyl]phenoxy}isobutyrate, 70 ml of ethanol and 12 ml of 1N sodium hydroxide solution are introduced into a round-bottomed flask equipped with a magnetic stirrer. The whole is heated under reflux for 1 hour 30 minutes, then cooled, neutralised with 12 ml of 1N hydrochloric acid solution and concentrated to dryness. The residue is taken up in ether. The whole is washed with water, dried over sodium sulphate and concentrated to dryness. The residue is chromatographed on 300 ml of Amicon silica (0.035-0.070 mm) while eluting first with pure dichloromethane and then with a mixture of dichloromethane and methanol (97:3).

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureThe whole is heated
  3. temperatureunder reflux for 1 hour 30 minutes
  4. temperaturecooled
  5. concentrationconcentrated to dryness
  6. washThe whole is washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated to dryness
  9. customThe residue is chromatographed on 300 ml of Amicon silica (0.035-0.070 mm)
  10. washwhile eluting first with pure dichloromethane
  11. additionwith a mixture of dichloromethane and methanol (97:3)

Sources & evidence

ORD record
ord-47ac9fe8c5c74ebea580b471971622e8
Source dataset
uspto-grants-1997_05
Patent number
US05627205

Reaction notes

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