Ethanol → Ethyl 4-chloro-3-(trifluoromethyl)benzoate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:20][CH3:21])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
A solution of 4-chloro-3-trifluoromethyl benzoic acid (10 g, 44.5 mmol) in ethanol (10 ml) was split equally between two microwave vials. Concentrated sulfuric acid (0.75 ml) was added to each vial (1.5 ml in total). The reactions were heated in the microwave at 120° C. for 30 minutes in total. The reaction mixtures were combined and concentrated in vacuo. The residue was partitioned between EtOAc (100 ml) and aq. sodium bicarbonate (100 ml), the organic phase was separated, washed with aq. sodium bicarbonate (100 ml) and water (2×100 ml) and then dried (phase separator) and the solvent removed in vacuo to give the title compound (4.126 g) as a colourless oil. δH (400 MHz, methanol-d4) consistent with previous example.
Workup
- customThe reaction mixtures
- concentrationconcentrated in vacuo
- customThe residue was partitioned between EtOAc (100 ml) and aq. sodium bicarbonate (100 ml)
- customthe organic phase was separated
- washwashed with aq. sodium bicarbonate (100 ml) and water (2×100 ml)
- customdried (phase separator)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-20b0126d55df4456a789bd4644683de4
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324254B2
Reaction notes
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