Water → HCID 20306501, compound
Reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:4]([O:6]C)=[O:5].[OH-].[K+].O.S(=O)(=O)(O)O>COCCOC>[CH3:1][S:2][CH:3]([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:4]([OH:6])=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl α-methylthio(3-thienyl)acetate (5.045 g) was dissolved in 60 ml of 1,2-dimethoxyethane, and 20 ml of a 2N aqueous solution of potassium hydroxide was added. The mixture was stirred at room temperature for 3 hours and 10 minutes. To the reaction mixture were added 30 ml of water and 6 ml of 3N sulfuric acid. The mixture was extracted three times with 50 ml of diethyl ether. The ethereal layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Recrystallization of the residue from benzene/n-hexane afforded 3.291 g of α-methylthio(3-thienyl)acetic acid as pale yellow crystals having a melting point of 73.5 to 74.0° C.
Workup
- extractionThe mixture was extracted three times with 50 ml of diethyl ether
- dry with materialThe ethereal layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customRecrystallization of the residue from benzene/n-hexane
Sources & evidence
- ORD record
- ord-fcd81c306511495da212da29d400e8a2
- Source dataset
- uspto-grants-1979_01
- Patent number
- US04137406
Reaction notes
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