Sodium Hydroxide → HCID 22118449, compound

HRID 1275464Notes

Reaction equation

HRID 1275464 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11](=[O:12])[C:10]2[C:5](=[C:6](Cl)[CH:7]=[C:8]([C:14]([O:16]CC)=[O:15])[C:9]=2[CH3:13])[S:4](=[O:21])(=[O:20])[CH2:3]1.[OH-].[Na+]>C(O)C.[Zn]>[CH3:1][C:2]1([CH3:22])[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([OH:16])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:21])(=[O:20])[CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22118459HCID 22118459, compound

Product 1

HCID 22118449HCID 22118449, compoundYield 116.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4.6 Grams (13 mmol) of 3,3,5-trimethyl-6-ethoxycarbonyl-8-chlorothiochroman-4-one-1,1-dioxide was dissolved in 35 ml of ethanol, and 3.3 g (83 mmol/20 ml) of a sodium hydroxide aqueous solution was added. The mixture was refluxed for 30 minutes. The reaction mixture was allowed to cool to 60° C., 2.6 g (40 mg atom) of a zinc powder was added, and the mixture was heated at 60° C. for 3.5 hours. The reaction mixture was allowed to cool to room temperature, an insoluble substance was filtered off, and the filtrate was cooled in an ice bath. To the filtrate was added 5 wt % hydrochloric acid to adjust a pH of 1, and the mixture was extracted with 100 ml of ethyl acetate twice. An organic layer was washed with 50 ml of water and dried over sodium sulfate, and the solvent was distilled off. The residue was dried under reduced pressure to give 4.3 g (yield 100%) of a hygroscopic yellowish amorphous solid.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperaturethe mixture was heated at 60° C. for 3.5 hours
  3. temperatureto cool to room temperature
  4. filtrationan insoluble substance was filtered off
  5. temperaturethe filtrate was cooled in an ice bath
  6. additionTo the filtrate was added 5 wt % hydrochloric acid
  7. extractionthe mixture was extracted with 100 ml of ethyl acetate twice
  8. washAn organic layer was washed with 50 ml of water
  9. dry with materialdried over sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-db6c8cfe7f5147ae93515528f9bf3464
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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