Potassium Hydroxide → HCID 23450690, compound

HRID 964393Notes

Reaction equation

HRID 964393 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:16]([O:18]CC)=[O:17])[C:5]([CH3:15])=[C:6]2[C:11]=1[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][CH:7]2[OH:14].[OH-].[K+]>C(O)C.[Zn]>[OH:14][CH:7]1[C:6]2[C:11](=[CH:2][CH:3]=[C:4]([C:16]([OH:18])=[O:17])[C:5]=2[CH3:15])[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23450669HCID 23450669, compound

Product 1

HCID 23450690HCID 23450690, compoundYield 143.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

10.0 g (31.3 mmol) of the 8-chloro-6-ethoxycarbonyl-4-hydroxy-5-methylthiochroman-1,1-dioxide obtained in the above step (7) was dissolved in 30 ml of ethanol, and 50 ml of a 16% potassium hydroxide aqueous solution and 6.1 g (93.3 mmol, 3.0 equivalents) of a zinc powder were added. The mixture was stirred under heat at 50° C. for 3 hours. After the completion of the reaction, the zinc powder was filtered off. While the reaction mixture was cooled, a 2N hydrochloric acid aqueous solution was added until the mixture had a pH of 1. Then, the mixture was extracted with ethyl acetate twice. An organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off to give 11.5 g (yield 100%) of 4-hydroxy-5-methylthiochroman-6-carboxylic acid-1,1-dioxide.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe zinc powder was filtered off
  3. temperatureWhile the reaction mixture was cooled
  4. additiona 2N hydrochloric acid aqueous solution was added until the mixture
  5. extractionThen, the mixture was extracted with ethyl acetate twice
  6. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cba1a88206444002804cda66dfbb3047
Source dataset
uspto-grants-1998_06
Patent number
US05767289

Reaction notes

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