ChemicalBook CAS DataBase List 2-Methyl-3-biphenylmethanol

2-Methyl-3-biphenylmethanol synthesis

10synthesis methods

Product Name:2-Methyl-3-biphenylmethanol
CAS Number:76350-90-8
Molecular formula:C14H14O
Molecular Weight:198.26

Carrying out a Suzuki coupling reaction between 3-bromo-2-methylbenzoic acid and phenyl substituted boric acid or phenyl substituted borate to obtain 3-phenyl-2-methylbenzoic acid, and then carrying out a reduction reaction to obtain 2-Methyl-3-biphenylmethanol, wherein the Suzuki coupling reaction is carried out at 10-150 DEG C for 1-12 hours under the action of an alkali. 3-phenyl-2-methylbenzoic acid can be directly reduced with a reducing agent such as borane and lithium aluminium hydride to obtain 2-Methyl-3-biphenylmethanol.

83647-43-2 Synthesis

83647-43-2
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$8.00/250mg

98-80-6 Synthesis

98-80-6
713 suppliers
$5.00/5g

76350-90-8
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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

83647-43-2 Synthesis

83647-43-2
119 suppliers
$8.00/250mg

76350-90-8
250 suppliers
$13.43/1gm:

References

84541-46-8 Synthesis

1-(chloromethyl)-2-methyl-3-phenyl-benzene

84541-46-8
13 suppliers
$160.00/0.500g

76350-90-8
250 suppliers
$13.43/1gm:

References

89951-60-0 Synthesis

89951-60-0
37 suppliers
$45.00/50mg

76350-90-8
250 suppliers
$13.43/1gm:

References

502483-86-5
0 suppliers
inquiry

76350-90-8
250 suppliers
$13.43/1gm:

References

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