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ChemicalBook CAS DataBase List Benzenebutanoic acid, 4-carboxy-, -alpha--ethyl ester (9CI)

Benzenebutanoic acid, 4-carboxy-, -alpha--ethyl ester (9CI) synthesis

3synthesis methods
177736-20-8 Synthesis
ethyl 4-(4-formylphenyl)butanoate

177736-20-8
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Benzenebutanoic acid, 4-carboxy-, -alpha--ethyl ester (9CI)

177736-21-9
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Yield:177736-21-9 84%

Reaction Conditions:

in isopropyl alcohol;acetone;

Steps:

31 31G 4-(3-Ethoxycarbonylpropyl)benzoic acid

31G 4-(3-Ethoxycarbonylpropyl)benzoic acid 1 ml of Jones's reagent was added at 0°C to a solution of ethyl 4-(4-formylphenyl)butanoate (1.16 g, 5.29 mmol) in acetone (7 ml). The reaction mixture was stirred at room temperature for 18 h, then added with isopropanol (1 ml) and extracted with ethyl ether. The organic phase was dried and the solvent was evaporated off, to obtain 1.05 g of the title compound as a colourless oil (84% yield). 1H N.M.R. (300 MHz, CDCl3) δ ppm: 1.09 (t, 3H); 1.81 (m, 2H); 2.17 (t, 2H); 2.55 (t, 2H); 3.97 (q, 2H); 7.11 (d, 2H); 7.87 (d, 2H); 9.11 (m, 1H).

References:

EP775133,2001,B1