4-Nitro-1-naphthol synthesis
- Product Name:4-Nitro-1-naphthol
- CAS Number:605-62-9
- Molecular formula:C10H7NO3
- Molecular Weight:189.17
86-57-7
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$14.00/5g
605-62-9
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$15.00/1g
Yield:605-62-9 90%
Reaction Conditions:
Stage #1: 1-Nitronaphthalenewith potassium hydroxide in water;dimethyl sulfoxide at 0 - 5; for 0.0833333 h;
Stage #2: with tert.-butylhydroperoxide in water;dimethyl sulfoxide at 20; for 2 h;
Steps:
1 5.1.1
4-Nitronaphthalen-1-ol (2)
To a solution of compound 1 (0.86 g, 5 mmol) in 13 mL of DMSO, was added a solution of KOH (1.2 g, 20 mmol) in water (5 mL) at 0-5 °C.
The mixture was stirred for 5 min before t-BuOOH (1.8 g, 10 mmol) in DMSO (2 mL) was added [36,37].
After stirring at room temperature for 2 h, the mixture was poured into 1 N HCl (50 mL) slowly, with yellow solid separation.
Crude product compound 2 was obtained after filtering to remove aqueous phase and then being allowed to dry in air.
The crude product was at last recrystallized with ethyl acetate/petroleum ether to give 0.76 g of title compound 2 as a faint yellow powder. Yield: 90%, mp: 166-168 °C. 1H NMR (DMSO-d6) δ 7.00 (d, J = 9.00 Hz, 1H, aromatic H), 7.65 (t, J = 7.20 Hz, 1H, aromatic H), 7.82 (t, J = 7.20 Hz, 1H, aromatic H), 8.34 (d, J = 9.00 Hz, 1H, aromatic H), 8.42 (d, J = 9.00 Hz, 1H, aromatic H), 8.67 (d, J = 9.00 Hz, 1H, aromatic H), 11.95 (s, 1H, phenolic OH). ESI-MS m/z 190.4 [M + H]+.
References:
Xu, Fuming;Jia, Yuping;Wen, Qingli;Wang, Xuejian;Zhang, Lei;Zhang, Yingjie;Yang, Kanghui;Xu, Wenfang [European Journal of Medicinal Chemistry,2013,vol. 64,p. 377 - 388]
90-15-3
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$9.00/5g
605-62-9
172 suppliers
$15.00/1g
776-34-1
171 suppliers
$8.00/1g
605-62-9
172 suppliers
$15.00/1g
