2,6-DiMethylbiphenyl-3-carboxylic acid synthesis

4synthesis methods

Product Name:2,6-DiMethylbiphenyl-3-carboxylic acid
CAS Number:955929-56-3
Molecular formula:C15H14O2
Molecular Weight:226.27

691905-26-7 Synthesis

691905-26-7
31 suppliers
$45.00/50mg

955929-56-3
10 suppliers
$175.00/100mg

Yield:955929-56-3 76%

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate;2-methyl-but-2-ene in tetrahydrofuran;water;tert-butyl alcohol at 0 - 20; for 3 h;

Steps:

2',6'-dimethyl-[1,1'-biphenyl]-3-carboxylic acid (8a)

To a solution of 7a (1 g, 4.8 mmol) in t-BuOH (3 mL) and THF (3 mL) were added 2-methylbut-2-ene (0.43 ml, 39 mmol) and NaH2PO4 (2.7 g, 20 mmol) at 0 °C. Then NaClO2 (1.24 g, 13.7 mmol) and H2O (0.5 mL) were added sequentially. The resulting mixture was stirred at room temperature for 3 h. The reaction was quenched by the addition of brine (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to furnish the crude residue, which was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v, 1% acetic acid was added) as eluent to afford the product 8a (0.82 g, 76%) as a white solid.1H NMR (300 MHz, DMSO-d6) δ: 12.72 (brs, 1H), 7.88-7.92 (m, 1H), 7.66-7.68 (m, 1H), 7.61 (t, J = 7.5 Hz, 1H), 7.43-7.47 (m, 1H), 7.12-7.24 (m, 3H), 2.02 (s, 6H).

References:

Yang, Jianyong;Li, Zheng;Li, Huilan;Liu, Chunxia;Wang, Nasi;Shi, Wei;Liao, Chen;Cai, Xingguang;Huang, Wenlong;Qian, Hai [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 8,p. 2445 - 2450] Location in patent:supporting information

[1,1'-Biphenyl]-3-carboxylic acid, 2',6'-dimethyl-, ethyl ester

955929-55-2
0 suppliers
inquiry

955929-56-3
10 suppliers
$175.00/100mg

References

3132-99-8 Synthesis

3132-99-8
474 suppliers
$5.00/10g

955929-56-3
10 suppliers
$175.00/100mg

References

100379-00-8
289 suppliers
$8.00/1g

955929-56-3
10 suppliers
$175.00/100mg

References