1-Octanol, 8-bromo- → 8-(3-Nitro-4-phenylphenoxy)octan-1-ol
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:16])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:16][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
3-Nitro-4-phenylphenol (860 mg, 4.0 mmol) was dissolved in N,N-dimethylformamide (40 mL), followed by addition of 8-bromo-1-octanol (1.86 g, 6.0 mmol). After stirring at 50° C. for 5 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 8-(3-nitro-4-phenylphenoxy)octan-1-ol (1.23 g).