Ethanol → Ethyl [4-(methylsulfanyl)phenyl]acetate
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH:7][CH:8]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-(methylthio)phenylacetic acid (5.10 g, 28.0 mmol) and H2SO4 (0.155 mL, 2.80 mmol) in EtOH (150 mL) in a 500 mL round bottom flask, were stirred at 100° C. for 26 hours. The reaction was concentrated in vacuo, diluted with EtOAc (200 mL), washed with deionized water (2×150 mL), and then with brine (100 mL). The organic layer was dried over MgSO4, concentrated, and dried in vacuo. The crude product was purified by flash column chromatography (silica, 0-20% EtOAc in hexane) to give the title compound (5.95 g). MS m/e=211 (M+H)+.
Workup
- concentrationThe reaction was concentrated in vacuo
- additiondiluted with EtOAc (200 mL)
- washwashed with deionized water (2×150 mL)
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
- customdried in vacuo
- customThe crude product was purified by flash column chromatography (silica, 0-20% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-be8343f4ed114698a6d959cb3bccd7cf
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928139B2
Reaction notes
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