Methanol → Methyl (3-(trifluoromethyl)phenyl)acetate
Reaction equation
[OH-:1].[Na+].Cl[C:4](Cl)(Cl)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.S(=O)(=O)(O)O.[CH3:23][OH:24]>>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:24][CH3:23])=[O:1])[CH:11]=[CH:10][CH:9]=1Participants
Procedure
Fifty ml. of methanol, 4.9 g. of sodium hydroxide and 6.0 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane were combined, and stirred under reflux for 6 hours. The mixture was cooled overnight, and was then made acid with 2.5 ml. of concentrated sulfuric acid. It was stirred under reflux for 1 hour more, cooled and filtered. The solids were washed with 100 ml. of methanol. Thirty ml. of water was added to the filtrate, and the aqueous layer was separated and washed 3 times with 20 ml. portions of dichloromethane. All of the organics were combined, and washed with two 15 ml. portions each of water and saturated sodium chloride. The organics were then dried over sodium sulfate and evaporated under vacuum to obtain 4.6 g. of an oil, which was found to contain 94% of the desired product by vapor phase chromatography.
Workup
- temperatureunder reflux for 6 hours
- temperatureThe mixture was cooled overnight
- stirringIt was stirred
- temperatureunder reflux for 1 hour more
- temperaturecooled
- filtrationfiltered
- washThe solids were washed with 100 ml
- additionof water was added to the filtrate
- customthe aqueous layer was separated
- washwashed 3 times with 20 ml
- washwashed with two 15 ml
- dry with materialThe organics were then dried over sodium sulfate
- customevaporated under vacuum
- customto obtain 4.6 g
Sources & evidence
- ORD record
- ord-f80a1bb961d144c3ad321673285d05aa
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04426536
Reaction notes
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