Method for preparing hydroxy-substituted polycyclic aromatic compound
A technology of aromatic compounds and biscarbonyl compounds, applied in the field of organic synthesis
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Embodiment 1a
[0030] Example 1a Synthesis of 10-phenyl-9phenanthrene
[0031] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazine, 6ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:
[0032]
[0033] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:
[0034] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,12...
Embodiment 1b
[0035] Example 1b Synthesis of 10-phenyl-9phenanthrene
[0036] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazine, 10ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:
[0037]
[0038] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:
[0039] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,1...
Embodiment 1c
[0040] Example 1c Synthesis of 10-phenyl-9phenanthrene
[0041] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazide, 15ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:
[0042]
[0043] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:
[0044] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,1...
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