ChemicalBook CAS DataBase List 2-nitro-5-phenyl-phenol

2-nitro-5-phenyl-phenol synthesis

5synthesis methods

Product Name:2-nitro-5-phenyl-phenol
CAS Number:18062-89-0
Molecular formula:C12H9NO3
Molecular Weight:215.2

580-51-8
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18062-89-0
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21419-75-0
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21419-74-9
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Yield:18062-89-0 26% ，21419-74-9 14% ，21419-75-0 41%

Reaction Conditions:

with nitric acid in acetic acid at 20; for 0.5 h;Cooling with ice;

Steps:

26 5.1.26 2-Nitrobiphenyl-3-ol (42), 4-nitrobiphenyl-3-ol (43) and 6-nitrobiphenyl-3-ol (44)

To a solution of 3-phenylphenol (6.00 g, 35.3 mmol) in AcOH (35 mL) was added dropwise 6 N HNO₃ solution (6.00 mL, 36.0 mmol) with cooling in an ice bath, and stirred at room temperature for 30 min. Water was then added, and the mixture was extracted with CH₂Cl₂. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica gel column chromatography using hexane/EtOAc (10:1 to 1:1, v/v) as eluent to give 43(1.96 g, 26%) as a yellow solid and a mixture of 42 and 44 as a brown oil. A mixture of 42 and 44 was purified by silica gel column chromatography using CHCl₃/MeOH (50:1, v/v) as eluent to give 42 (1.08 g, 14%) as a brown solid and 44 (3.11 g, 41%) as a brown oil. 42: mp 81-83 °C [lit.^22a: 85-86 °C (benzene)]; ¹H NMR (400 MHz, CDCl₃) δ 9.54 (1H, s), 7.49 (1H, t, J = 7.9 Hz), 7.42-7.40 (3H, m), 7.27-7.25 (2H, m), 7.15 (1H, dd, J = 7.4, 1.3 Hz), 6.90 (1H, dd, J = 7.4, 1.3 Hz); IR (ATR) 1593, 1525, 1350, 1296, 1211 cm^-1; HRMS (ESI) m/z calcd for C₁₂H₈NO₃ [M-H]^- 214.0510; found 214.0505; 43: mp 103-105 °C (EtOH) [lit.^22a: 104-105 °C (EtOH)]; ¹H NMR (400 MHz, CDCl₃) δ 10.71 (1H, s), 8.17 (1H, d, J = 8.8 Hz), 7.63-7.62 (2H, m), 7.53-7.42 (3H, m), 7.38-7.35 (1H, m), 7.22 (1H, dd, J = 8.8, 1.7 Hz); IR (ATR) 2362, 616, 1574, 1277, 1169 cm^-1; HRMS (ESI) m/z calcd for C₁₂H₈NO₃ [M-H]^- 214.0510; found 214.0505; 44: ¹H NMR (400 MHz, CDCl₃) δ 7.92 (1H, d, J = 8.8 Hz), 7.40-7.39 (3H, m), 7.28-7.26 (2H, m), 6.86-6.83 (1H, m), 6.79 (1H, d, J = 2.7 Hz), 6.02 (1H, s); IR (ATR) 3365, 1574, 1508, 1308, 1201 cm^-1; HRMS (ESI) m/z calcd for C₁₂H₈NO₃ [M-H]^- 214.0510; found 214.0505.

References:

Fukaya, Takayuki;Kodo, Toru;Ishiyama, Takeo;Kakuyama, Hiroyoshi;Nishikawa, Hiroyuki;Baba, Satoko;Masumoto, Shuji [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 18,p. 5568 - 5582]

580-51-8
155 suppliers
$111.00/5g

18062-89-0
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References

92-93-3 Synthesis