Formamide → 2,4,6-Trimethoxybenzaldehyde
Reaction equation
C(N)=[O:2].[CH3:4][O:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:7]=1[CH2:8]NC=O>C(O)=O>[CH3:4][O:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:7]=1[CH:8]=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
1.96 g (10 mmol) of XII, 20 ml of formamide, and 2 ml of formic acid were placed in the GreenChem reaction vessel. The GreenChem reaction vessel was placed into the MARS-5 reaction system and the reaction mixture was quickly heated to 200° C. The reaction mixture was kept at 200° C. for 3 minutes and then cooled to 100° C. The GreenChem reaction vessel was removed from the MARS 5 system, the residual pressure was released, and the reaction vessel was opened. TLC showed that the reaction was complete. The reaction mixture was cooled to room temperature; the precipitated crystals were separated by filtration, rinsed with water and dried with vacuum. The filtrate was used as solvent in the next reaction. The reaction was repeated 10 times. The total of 9.6492 g of formic acid, and 34.5680 g of formamide were added to the reaction mixture over the ten cycles to compensate the losses. The total yield of 2,4,6-trimethoxybenzylformamide (XIII) is quantitative.
Workup
- customThe GreenChem reaction vessel
- customwas placed into the MARS-5 reaction system
- temperaturecooled to 100° C
- customThe GreenChem reaction vessel
- customwas removed from the MARS 5 system
- temperatureThe reaction mixture was cooled to room temperature
- customthe precipitated crystals were separated by filtration
- washrinsed with water
- customdried with vacuum
- customThe filtrate was used as solvent in the next reaction
Sources & evidence
- ORD record
- ord-27b5cb0264ad4c9b9b11dfd15a7bbc56
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710268B2
Reaction notes
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