ChemicalBook CAS DataBase List 4-(PENTYLOXY)-4'-BIPHENYLCARBOXYLIC ACID

4-(PENTYLOXY)-4'-BIPHENYLCARBOXYLIC ACID synthesis

7synthesis methods

Product Name:4-(PENTYLOXY)-4'-BIPHENYLCARBOXYLIC ACID
CAS Number:59748-15-1
Molecular formula:C18H20O3
Molecular Weight:284.35

110-53-2 Synthesis

110-53-2
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$13.69/5g

58574-03-1 Synthesis

58574-03-1
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$5.00/250mg

4-(PENTYLOXY)-4'-BIPHENYLCARBOXYLIC ACID

59748-15-1
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$272.00/1g

Yield:59748-15-1 76.6%

Reaction Conditions:

Stage #1: 1-Bromopentane;4'-Hydroxybiphenyl-4-carboxylic acidwith 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:experimental part