2-Methyl-3-biphenylmethanol synthesis
- Product Name:2-Methyl-3-biphenylmethanol
- CAS Number:76350-90-8
- Molecular formula:C14H14O
- Molecular Weight:198.26
83647-43-2
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Yield:76350-90-8 98%
Reaction Conditions:
with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct;Sodium hydrogenocarbonate in ethanol;toluene at 80; for 3 h;Inert atmosphere;
Steps:
(2-Methyl-[1,1'-biphenyl]-3-yl) methanol (3)
A mixture of (3-bromo-2methylphenyl) methanol (1.00 g, 4.96 mmol), Phenylboronic acid (1.21 g, 9.92 mmol) and Pd(dppf)Cl2·CH2Cl2 (20.2 mg, 25.0 μmol) in ethanol (3.3 mL) and toluene (10 mL) was under argon. To the solution sodium bicarbonate, 2M (10 mL) was added and the mixture was heated at 80 °C for 3h. Then the mixture was diluted with EtOAc (100 mL) and washed with saturated NaCl solution (50 mL), dried over Na2SO4, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate 12:1) to afford compound 3 (1.07g, 98%) as white solid. M.p. 74-76 °C; IR (KBr): 3350, 3049, 1600, 1465, 1050,755 cm-1. 1H NMR (400 MHz, CDCl3) δ 7.47 - 7.20 (m, 8H), 4.78 (s, 2H), 2.25 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 142.9, 142.1, 139.2, 133.6, 129.5, 128.1, 126.8, 125.6, 77.1, 76.7, 64.1, 15.9. HRMS (ESI) calculated for C14H14NaO+ [M+Na]+: 221.0937, found 221.0939.
References:
Wang, Yubo;Zhou, Yuanyuan;Cao, Sheng;Sun, Yue;Dong, Zhiqiang;Li, Chen;Wang, Haoran;Yao, Yuhong;Yu, Haiyan;Song, Xiangyi;Li, Ming;Wang, Jiefu;Wei, Mingming;Yang, Guang;Yang, Cheng [Bioorganic Chemistry,2021,vol. 111,art. no. 104833] Location in patent:supporting information
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![2-Methyl-[1,1'-biphenyl]-3-carbaldehyde](/CAS/20180527/GIF/89951-60-0.gif)
89951-60-0
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76350-90-8
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