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

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

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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