N,N-dimethyl-p-phenylenediamine → 2,6-Di-tert-butyl-4[(4-dimethylamino-phenylamino)-methyl]-phenol
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1.[CH3:18][N:19]([CH3:27])[C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1>O1CCCC1>[C:9]([C:7]1[CH:8]=[C:3]([CH2:2][NH:26][C:23]2[CH:24]=[CH:25][C:20]([N:19]([CH3:27])[CH3:18])=[CH:21][CH:22]=2)[CH:4]=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:13])([CH3:12])([CH3:11])[CH3:10]Participants
Procedure
4-Bromomethyl-2,6-di-tert-butyl-phenol (2.42 g, 0.008 mole) was dissolved in 50 mL of dry tetrahydrofuran. In a separate conical flask N,N-dimethyl-benzene-1,4-diamine (2.17 g, 0.016 mole) was dissolved in 25 mL of tetrahydrofuran and solution was transferred to a cylindrical funnel with pressure equalizing tube. Three-necked round-bottom flask containing solution of 4-Bromomethyl-2,6-di-tert-butyl-phenol was kept in oil-bath at 85° C. Solution in the flask was continuously stirred with the help of magnetic stirrer. N, N-dimethyl-para-phenylene diamine solution was added drop-by-drop, from funnel to the flask in acidic medium for a span of 4-5 hours till all the solution was poured out. The reaction was terminated after that and the final reaction mixture was allowed to attain room temperature.
Workup
- customsolution was transferred to a cylindrical funnel with pressure
- customwas kept in oil-bath at 85° C
- additionwas poured out
- customThe reaction was terminated after that and the final
- customreaction mixture
- customto attain room temperature
Sources & evidence
- ORD record
- ord-9b3188972432436ba5a82a9cd5ca677e
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770785B1
Reaction notes
Loading…