Water → 2,3-DIFLUORO-6-HYDROXY-5-METHYLBENZALDEHYDE
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[CH2:11]1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O.[OH2:26]>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([OH:9])=[C:6]([C:7]=1[F:8])[CH:11]=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 98.5 °C
Procedure
30 g of 4,5-difluoro-2-methylphenol are dissolved in 180 ml of trifluoroacetic acid and admixed with 57.2 g of hexamethylenetetramine in portions. On completion of addition, the reaction solution is heated to 97-100° C. for 4 hours. After cooling, first 60 ml of 50% sulphuric acid and then 300 ml of water are added dropwise, then the solution is stirred further at room temperature for 2 hours. The reaction solution is extracted three times with methyl tert-butyl ether. The combined extracts are washed once with water and dried, and the solvent is distilled off under reduced pressure. The residue is extracted repeatedly with n-hexane, the extracts are combined and the solvent is distilled off under reduced pressure. 12.5 g (33% of theory) of a bright yellow solid are obtained having a melting point of 53-56° C.
Workup
- additionOn completion of addition
- temperatureAfter cooling
- extractionThe reaction solution is extracted three times with methyl tert-butyl ether
- washThe combined extracts are washed once with water
- customdried
- distillationthe solvent is distilled off under reduced pressure
- extractionThe residue is extracted repeatedly with n-hexane
- distillationthe solvent is distilled off under reduced pressure
- custom12.5 g (33% of theory) of a bright yellow solid are obtained
Sources & evidence
- ORD record
- ord-f84b9be902bb4a2ea79349d91993657f
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903239B2
Reaction notes
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