Triphenylamine → Benzaldehyde, 4-(diphenylamino)-
Reaction equation
O=P(Cl)(Cl)Cl.[C:6]1([N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.O.O.[C:28]([O-])(=[O:30])C.[Na+]>CC(C)=O>[C:19]1([N:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:13]2[CH:18]=[CH:17][C:16]([CH:28]=[O:30])=[CH:15][CH:14]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
30 mL of dimethylformaldehyde (DMF) was put into a 250 mL flask, cooled to 0° C. and 3.8 mL of POCl3 was slowly added thereto. Then, 10 g of triphenylamine was added to the resultant mixture and heated to 70° C. for 5 hours. The reaction container was cooled to room temperature and then a reactant solution was poured into ice water. Subsequently, 40 g of sodium acetate trihydrate was put for neutralization and then an organic layer was separated with methylenechloride. The obtained organic layer was dried using magnesium sulfate and methylenechloride was removed under reduced pressure, yielding a product. The product was recrystallized using methanol and a light yellow solid was finally obtained, yielding 73% of a desired product. Data of NMR spectra confirmed that the product had the same structure as 4-(diphenylamino)benzaldehyde, that is, the compound (1) in the reaction scheme 2.
Workup
- temperatureheated to 70° C. for 5 hours
- temperatureThe reaction container was cooled to room temperature
- customan organic layer was separated with methylenechloride
- customThe obtained organic layer was dried
- customwas removed under reduced pressure
- customyielding a product
- customThe product was recrystallized
- customa light yellow solid was finally obtained
Sources & evidence
- ORD record
- ord-2127450570684b90b793a3eb38c01bd1
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878468B2
Reaction notes
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