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 g, 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 ether (150 ml), washed with saturated aqueous NaHCO3, dried (Na2SO4), and evaporated to afford the title compound (10.5 g, 100%), as a colourless oil, 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 ether (150 ml)
- washwashed with saturated aqueous NaHCO3
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-6988336624c44668a75cfa8d1f19a0cf
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665883
Reaction notes
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