2-Aminophenol → Salicylaldehyde
Reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].N[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].[OH-].[Na+]>O>[CH:8](=[O:9])[C:12]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
3.3 g of 3-aminophenol, 7.0 g of 2-ethylhexyl bromide and 2.0 g of calcium carbonate powder were mixed together with 10 g of dimethylformamide and reacted in a nitrogen atmosphere at 120° C. for 2 hours. Then, 6.4 g of n-octyl bromide was added to the reaction system, and the reaction was further continued for 5 hours under the above conditions. After the reaction, the reaction mixture was returned to room temperature and extracted with toluene to obtain 3-(N-octyl-N-2-ethylhexyl)aminophenol. Then, 11 g of phosphorus oxychloride was added to 13 g of dimethylformamide and stirred for one hour at a temperature of not higher than 15° C., and then the above aminophenol derivative was dropwise added and mixed thereto, and the reaction was carried out at a reaction temperature of 70° C. for 1.5 hours. The reaction product was returned to room temperature, and then put into water containing 8.6 g of sodium hydroxide to obtain a corresponding salicylaldehyde derivative. Then, into 20 g of ethanol, 4.0 g of 2-benzothiazolylacetic acid ethyl ester, 7.7 g of the above salicylaldehyde derivative and 0.5 g of piperidine were mixed and dissolved and reacted at 80° C. for one hour to obtain the desired product as yellowish orange crystals.
Workup
- additionmixed
- waitthe reaction was carried out at a reaction temperature of 70° C. for 1.5 hours
- customwas returned to room temperature
Sources & evidence
- ORD record
- ord-2501d2cbbfd5450885eecc44ba0091a4
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05738974
Reaction notes
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