Hexamethylenetetramine → Methyl 5-formyl-2-methoxybenzoate
Reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[CH:25]([C:6]1[CH:5]=[CH:4][C:3]([O:8][CH3:9])=[C:2]([CH:7]=1)[C:1]([O:11][CH3:12])=[O:10])=[O:26]Participants
Procedure
16.6 g of methyl o-anisate was dissolved in 100 ml of trifluoroacetic acid. Thereto was added 14.0 g of hexamethylenetetramine with ice-cooling. The mixture was refluxed for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was poured into 120 ml of water. The mixture was neutralized with sodium hydrogencarbonate and then extracted with ethyl acetate. The extract was washed with water and a saturated aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=2/1) to obtain 16.1 g of methyl 5-formyl-2-methoxybenzoate. It was recrystallized from diisopropyl ether to obtain 14.0 g of colorless crystals having a melting point of 85°-86° C.
Workup
- temperaturecooling
- temperatureThe mixture was refluxed for 2 hours
- customThe solvent was removed by distillation under reduced pressure
- additionThe residue was poured into 120 ml of water
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materiala saturated aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-9d5ebefa652d4516ab19f40af1285539
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948796
Reaction notes
Loading…