Methanol → alpha-Phenylthio-2-thiopheneacetic acid
Reaction equation
[OH-:1].[K+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=O.C(Cl)(Cl)Cl.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:21][OH:22]>>[C:14]1([S:20][CH:8]([C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:21]([OH:22])=[O:1])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Procedure
6.80 g (103 mmols) of potassium hydroxide (85% purity) was dissolved in 20 ml of methanol, and the resulting solution was added dropwise to a solution of 2.24 g (20.0 mmols) of thiophenealdehyde, 3.5 g (30.0 mmols) of chloroform and 3.30 g (30 mmols) of thiophenol in 10 ml of methanol over a period of 30 minutes at room temperature. The resulting reaction mixture was stirred at room temperature for 1 hour, and heated while refluxing for 1 hour. Most of the solvent was removed by distillation under reduced pressure, and the residue was dissolved in water. The solution was rendered acidic with hydrochloric acid, and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography eluting with diethyl ether-hexane (1:5 by volume) to obtain 2.03 g (41% yield) of α-phenylthiothiophene-2-acetic acid.
Workup
- customThe resulting reaction mixture
- temperatureheated
- temperaturewhile refluxing for 1 hour
- customMost of the solvent was removed by distillation under reduced pressure
- dissolutionthe residue was dissolved in water
- extractionextracted with methylene chloride
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- custompurified by silica gel column chromatography
- washeluting with diethyl ether-hexane (1:5 by volume)
Sources & evidence
- ORD record
- ord-dba0232fe8be4cc1b5404907a684d1e4
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04245108
Reaction notes
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