4-Hydroxybenzaldehyde → 4-(2,2,3,3-Tetrafluoropropoxy)benzaldehyde
Reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[H][H].C1(C)C=CC(S(O[CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])(=O)=O)=CC=1>CCCCCC.CN(C)C(=O)C.C1C=CC=CC=1.CCCCCC>[F:29][C:25]([F:30])([CH:26]([F:28])[F:27])[CH2:24][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
After 1.90 g (43.5 mmol) of 55% sodium hydride were washed with hexane, it was suspended in 25 ml of N,N-dimethylacetamide and 5.3 g (43 mmol) of 4-hydroxybenzaldehyde were gradually added to the suspension at 0° C. under nitrogen atmosphere. When generation of hydrogen gas stopped, 11.14 g (39 mmol) of 2,2,3,3-tetrafluoropropyl p-toluenesulfonate were added to the reaction mixture, followed by heating of the resulting mixture at 120° C. with stirring for 2 hours and 15 minutes. After the reaction mixture was cooled, a mixed solvent of benzene-hexane (1:1) was added thereto and the resulting mixture was washed with water. After drying, the solvent was distilled off to obtain 8.85 g (yield: 96%) of the title compound as an oil.
Workup
- temperatureAfter the reaction mixture was cooled
- washthe resulting mixture was washed with water
- customAfter drying
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-d5fc30813830435db040a2e57c866246
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300357B1
Reaction notes
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