ChemicalBook CAS DataBase List 4-N-OCTYLOXYBIPHENYL-4'-CARBOXYLIC ACID

4-N-OCTYLOXYBIPHENYL-4'-CARBOXYLIC ACID synthesis

13synthesis methods

Product Name:4-N-OCTYLOXYBIPHENYL-4'-CARBOXYLIC ACID
CAS Number:59748-18-4
Molecular formula:C21H26O3
Molecular Weight:326.43

111-83-1 Synthesis

111-83-1
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$12.00/25g

58574-03-1 Synthesis

58574-03-1
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$5.00/250mg

59748-18-4
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$36.39/1g

Yield: 73.5%

Reaction Conditions:

Stage #1:1-bromo-octane;4'-Hydroxybiphenyl-4-carboxylic acid with potassium hydroxide in ethanol;water for 24 h;Inert atmosphere;Reflux;
Stage #2: with hydrogenchloride in ethanol;water; pH=6

Steps:

4.1.2. 4'-Pentyloxy-biphenyl-4-carboxylic acid (14a)
A solution of 4'-hydroxy-biphenyl-4-carboxylic acid (13) (5.0 g, 23.4 mmol) and KOH (5.3 g, 94.6 mmol) in EtOH/H₂O (10:1, 100 mL) was refluxed under N₂ for 30 min. Then, 1-bromopentane (7.06 g, 46.8 mmol) was added and the resulting mixture was refluxed for 24 h. After cooling, the pH value of the solution was adjusted to 6.0 by dilute HCl. The solid was filtered and recrystalized in MeOH and CH₂Cl₂ to afford 14a (5.08 g, yield 76.6%) as white solid. ¹H NMR (DMSO-d₆, 500 MHz) δ: 12.7 (s, 1H), 7.98 (d, 2H), 7.75 (d, 2H), 7.68 (d, 2H), 7.05 (d, 2H), 4.02 (t, 2H, J=6.5 Hz), 1.74 (m, 2H), 1.39 (m, 4H), 0.91 (t, 3H, J=7.2 Hz). MS (ESI⁺) m/z: 307.35 [M+Na⁺, 100%]. Anal. calcd for C₁₈H₂₀O₃: C, 76.06; H, 7.04; found: C, 75.25; H, 7.02. The synthetic procedure for compounds 14b was similar to the preparation of compound 14a except using 1-bromooctane instead of 1-bromopentane.³⁹

References:

Yao, Jianzhong;Liu, Hongming;Zhou, Ting;Chen, Hai;Miao, Zhenyuan;Dong, Guoqiang;Wang, Shengzheng;Sheng, Chunquan;Zhang, Wannian [Tetrahedron,2012,vol. 68,# 14,p. 3074 - 3085] Location in patent:supporting information; experimental part

52364-73-5 Synthesis