Hydrolysis of Ethyl 3-(1-pyrenyl)propanoate; 3-(1-Pyrenyl)propionic acid
Submitted Oct 06, 2011, published Oct 11, 2011
Anish Mistry (firstname.lastname@example.org
A contribution from
Fox Group, Warwick University
Ethyl 3-(1-pyrenyl)propanoate (1 equiv, prepared)
KOH (2 equiv, Fischer Scientific)
pH2 buffer solution (prepared)
Under a dinitrogen atmosphere, ethyl 3-(1-pyrenyl)propanoate (0.5 g, 1.6 mmol) was dissolved in warm ethanol (10 ml), then water (1 ml) and solid potassium hydroxide (0.18 g, 3.2 mmol) was added and the solution left stirring overnight. The reaction mixture was cooled and solvent removed under vacuo. Buffer solution (pH 2, 10 ml) was added and the mixture was extracted with ethyl acetate (10 ml x 3). The combined organics were dried over Na2SO4 and solvent was removed in vacuo to yield orange crystalline solid (0.45 g, 99%)
δH(400MHz, CDCl3) ppm: 2.94 (2H, t, J 8, CH2), 3.72 (2H, t, J 8, CH2), 7.92 (1H, d, J 8, aryl), 7.99 - 8.21 (7H, m, aryl), 8.28 (1H, d, J 9, aryl).
Ta-Hsien Chuang, Shiow-Ju Lee, Cheng-Wei Yang and Pei-Lin Wu, Expedient synthesis and structure–activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids, Org. Biomol. Chem., 2006, 4, 860–867
(1-Pyrenylmethyl)amino alcohols, a new class of antitumor DNA intercalators. Discovery and initial amine side chain structure-activity studies, Kenneth W. Bair, Richard L. Tuttle, Vincent C. Knick, Micheal Cory and David D. McKee, Journal of Medicinal Chemistry, 1990, 33(9), 2385-93.
Keywords: esters, hydrolysis