Potassium Hydroxide → HCID 23450690, compound
Reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[C:7](Cl)[CH:8]=[C:9]([C:13]([O:15]CC)=[O:14])[C:10]=2[CH3:12])[S:5](=[O:20])(=[O:19])[CH2:4][CH2:3]1.[OH-].[K+]>C(O)C.[Zn]>[OH:1][CH:2]1[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:20])(=[O:19])[CH2:4][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
10 Grams (31 mmol) of 4-hydroxy-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman-1,1-dioxide was dissolved in 30 ml of ethanol, and 50 ml of a 16 wt % potassium hydroxide aqueous solution and 6.1 g (93 mg atom, 3 eq.) 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 separated by filtration. While the reaction mixture was cooled, 2N hydrochloric acid aqueous solution was added to adjust a pH of 1. Then, the reaction 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 11.5 g (yield 100%) of 4-hydroxy-5-methyl-6-carboxythiochroman-1,1-dioxide.
Workup
- customAfter the completion of the reaction
- customthe zinc powder was separated by filtration
- temperatureWhile the reaction mixture was cooled
- addition2N hydrochloric acid aqueous solution was added
- extractionThen, the reaction mixture was extracted with ethyl acetate twice
- washAn organic layer was washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-dfe473a11b854085989bf8313d884ccc
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159904
Reaction notes
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