Hexamethylenetetramine → 4-Methoxy-3-(trifluoromethyl)benzaldehyde
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:9][CH3:10])[CH:25]=[O:26]Participants
4
Procedure
A mixture of 8.5 g 2-trifluoromethyl anisole and 7.0 g hexamethylene tetramine was stirred at 90° C. for 1.5 hr in 80 ml trifluoroacetic acid. The reaction solution was evaporated. The resulting residue was dissolved in ethyl acetate, and it was added dropwise into ice-cooled saturated aqueous sodium bicarbonate. The ethyl acetate layer was recovered and washed with brine. It was dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting residue was purified by silica gel column chromatography to give 5.8 g of 3-trifluoromethyl-p-anisaldehyde.
Workup
- customThe reaction solution was evaporated
- dissolutionThe resulting residue was dissolved in ethyl acetate
- additionit was added dropwise into ice-
- temperaturecooled saturated aqueous sodium bicarbonate
- customThe ethyl acetate layer was recovered
- washwashed with brine
- dry with materialIt was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7d66a26dace342fab01da025604cd74b
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699870B2
Reaction notes
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