HCID 23450700, compound → HCID 23450677, compound

HRID 964377Notes

Reaction equation

HRID 964377 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[C:7](Cl)[CH:8]=[C:9]([C:13]([OH:15])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:18])(=[O:17])[CH2:4][CH2:3]1>C(O)C.O.[Zn]>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]([OH:15])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:18])(=[O:17])[CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 23450700HCID 23450700, compound

Product 1

HCID 23450677HCID 23450677, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

0.88 Gram (2.90 mmol) of 4,4,5-trimethyl-8-chlorothiochroman-6-carboxylic acid-1,1-dioxide was dissolved in ethanol having a water content of 60%, 0.55 g (8.70 mmol) of a zinc powder was added, and the mixture was refluxed under heat for 5 hours. After the completion of the reaction, 50 ml of water was added, the zinc powder was removed by filtration, and the remainder was extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure to give 0.60 g (yield 78%) of 4,4,5-trimethylthiochroman-6-carboxylic acid-1,1-dioxide.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed
  3. temperatureunder heat for 5 hours
  4. additionwas added
  5. customthe zinc powder was removed by filtration
  6. extractionthe remainder was extracted with ethyl acetate
  7. washThe extract was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aac22df995fc4819ad239cfa9f48647e
Source dataset
uspto-grants-1998_06
Patent number
US05767289

Reaction notes

Loading…