ChemicalBook CAS DataBase List 4-(4-N-BUTYLPHENYL)BENZOIC ACID

4-(4-N-BUTYLPHENYL)BENZOIC ACID synthesis

5synthesis methods

Product Name:4-(4-N-BUTYLPHENYL)BENZOIC ACID
CAS Number:59662-46-3
Molecular formula:C17H18O2
Molecular Weight:254.32

[1,1'-Biphenyl]-4-carboxylic acid, 4'-butyl-, methyl ester

1451206-56-6

59662-46-3

General Method 13: Synthesis of biaryl or aryl-heteroaryl carboxylic acids from 1-bromo-4-butylbenzene and arylboronic or heteroarylboronic acids by Suzuki coupling reaction. This method is specifically applied to the synthesis of 4-n-butylbiphenyl-4'-carboxylic acids. A mixture of methyl 4-(4-butylphenyl)benzoate (89.0 g, 0.332 mol) and NaOH (26.6 g, 0.664 mol) in THF/H2O (500 mL/100 mL) mixed solvent was heated to reflux and reacted overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, THF was removed by distillation under reduced pressure.The residue was acidified to pH 3-4 with 2N HCl solution.The resulting mixture was filtered and the filter cake was washed with deionized water and dried to give 4-(4-butylphenyl)benzoic acid (60.0 g, yield: 71.1%) as white solid. The mass spectrum (ESI) showed m/z 255.0 ([M+H]+).

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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59662-46-3
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Yield: 71.1%

Reaction Conditions:

with water;sodium hydroxide in tetrahydrofuranReflux;

Steps:

151.13
[00269] General Method 13: The synthesis of a biaryl or aryl-heteroaryl carboxylic acid from l-bromo-4-butylbenzene and an aryl- or heteroaryl boronic acid. An illustration of this method is depicted for 4-(4-butylphenyl)benzoic acid. [00271] A mixture of methyl 4-(4-butylphenyl)benzoate (89.0 g, 0.332 mol), NaOH (26.6 g, 0.664 mol) in THF/H₂0 (500 mL/100 mL) was heated to reflux overnight. After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH -3-4 with 2 N HC1 solution. The resulting mixture was filtered and the cake was washed with water, dried to give 4-(4-butylphenyl)benzoic acid (60.0 g, yield: 71.1%), as a white solid. (ESI) m/z 255.0 (M + H)⁺.

References:

RQX PHARMACEUTICALS, INC.;HIGUCHI, Robert, I.;ROBERTS, Tucker, Curran;SMITH, Peter, Andrew;CAMPBELL, David;PARASELLI, Prasuna WO2013/123456, 2013, A1 Location in patent:Paragraph 00269; 00271