Water → HCID 15278551, compound

HRID 129432Notes

Reaction equation

HRID 129432 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:19]([OH:21])=[O:20])[C:5]([CH3:18])=[C:6]2[C:11]=1[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][CH:7]2[O:14][CH2:15][CH2:16][CH3:17].[OH-].[K+].O>[Zn].C(O)C>[CH2:15]([O:14][CH:7]1[C:6]2[C:11](=[CH:2][CH:3]=[C:4]([C:19]([OH:21])=[O:20])[C:5]=2[CH3:18])[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8]1)[CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 15278532HCID 15278532, compound

Product 1

HCID 15278551HCID 15278551, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A 50-ml egg-plant type flask was charged with 1.36 g (0.0041 mol) of 8-chloro-4-n-propoxy-5-methylthiochroman-6-carboxylic acid-1,1-dioxide, 1.35 g (0.02 mol) of potassium hydroxide, 0.81 g (0.012 mol) of a zinc powder, 10 ml of water and 6 ml of ethanol, and the mixture was refluxed under heat for 10 hours. After allowed to cool, insolubles were removed by filtration, and the ethanol was distilled off under reduced pressure. Then, while the remainder was cooled with ice, 50 ml of 5% hydrochloric acid was added to adjust the pH to 1. The reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 2% hydrochloric acid, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 1.0 g of 4-n-propoxy-5-methylthiochroman-6-carboxylic acid-1,1-dioxide (Compound 32) shown in Table 2.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 10 hours
  3. temperatureto cool
  4. custominsolubles were removed by filtration
  5. distillationthe ethanol was distilled off under reduced pressure
  6. temperatureThen, while the remainder was cooled with ice, 50 ml of 5% hydrochloric acid
  7. additionwas added
  8. extractionThe reaction mixture was extracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with 2% hydrochloric acid
  10. washwashed with a saturated sodium chloride aqueous solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-299075009b074fae91eb71a9468e416e
Source dataset
uspto-grants-1995_11
Patent number
US05468722

Reaction notes

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