Ethanol → 4-Ethylthio-5-methyl-6-carboxy-8-chlorothiochroman

HRID 1275463Notes

Reaction equation

HRID 1275463 reaction equation
[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[C:9]([Cl:20])[CH:10]=[C:11]([C:15]([O:17]CC)=[O:16])[C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1)[CH3:2].[OH-].[K+].C(O)C>O>[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[C:9]([Cl:20])[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 221184604-Ethylthio-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman

Product 1

HCID 221184154-Ethylthio-5-methyl-6-carboxy-8-chlorothiochromanYield 143.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.75 Gram (2.3 mmol) of 4-ethylthio-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman, 0.47 g (7.1 mmol) of potassium hydroxide, 5 ml of ethanol and 2 ml of water were mixed, and the mixture was stirred under heat at 60° C. for 2 hours. After the completion of the reaction, the solvent was distilled off, 5 ml of water was added, and then 2N hydrochloric acid was added to adjust 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 dried over anhydrous sodium sulfate, and the solvent was distilled off to give 1.0 g (yield 100%) of 4-ethylthio-5-methyl-6-carboxy-8-chlorothiochroman.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off
  3. addition5 ml of water was added
  4. addition2N hydrochloric acid was added
  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-b665cdf0909f4a83be29f089c20ea151
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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