Hydrochloric Acid → 4-(3,3,3-Trifluoropropoxy)benzoic acid
Reaction equation
[OH-:1].[K+].[F:3][C:4]([F:17])([F:16])[CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.OO.Cl>CO>[F:3][C:4]([F:16])([F:17])[CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]([OH:1])=[O:13])=[CH:10][CH:9]=1Participants
6
Conditions
- Temperature
- 65 °C
Procedure
To a stirred solution of 50% w/v KOH (0.8 ml) and 4-(3,3,3-trifluoropropoxy)benzaldehyde (0.4 g, 1.83 mmol) in MeOH (4 ml) at 65° C. was added dropwise over 20 min aqueous hydrogen peroxide (30 wt. % in water, 1.5 ml). On completion of the addition the reaction mixture was heated at 65° C. for a further 10 min. On cooling to room temperature, the reaction mixture was acidified with 1 M HCl and extracted with Et2O (3×25 ml). The combined organic extracts were washed with brine (25 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give the title compound (0.36 g, 83%) as a colourless solid which was used without further purification.
Workup
- customat 65° C.
- additionOn completion of the addition the reaction mixture
- temperatureOn cooling to room temperature
- extractionextracted with Et2O (3×25 ml)
- washThe combined organic extracts were washed with brine (25 ml)
- dry with materialdried (Na2SO4)
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-3ddbd9232e7c4b4c9a40e16e6fa7bf6c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895313B2
Reaction notes
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