Methanol → Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.S(Cl)(Cl)=O.[CH3:23]O>>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:23])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1Participants
4
Conditions
- Temperature
- 4 °C
Procedure
3,5-Bis(trifluoromethyl)phenylacetic acid (10.0 ·, 36.7 mmol), was dissolved in methanol (150 ml). The solution was cooled to 4° C. under an atmosphere of dry nitrogen, and thionyl chloride (10 ml) was added dropwise with vigorous stirring over 30 minutes. The mixture was warmed to room temperature, and then stirred for 1 hour. The solvents were evaporated at reduced pressure, the residue dissolved in diethyl ether (150 ml), washed with saturated aqueous NaHCO3, dried (Na2 SO4), and evaporated to afford the title compound (10.5 g, 100%), as a colourless oil which was used without further purification.
Workup
- temperatureThe mixture was warmed to room temperature
- stirringstirred for 1 hour
- customThe solvents were evaporated at reduced pressure
- dissolutionthe residue dissolved in diethyl ether (150 ml)
- washwashed with saturated aqueous NaHCO3
- customdried (Na2 SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-ad29175b0ba74090ad4fee5a58c3be99
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05760018
Reaction notes
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