Uses
4-(p-Iodophenyl)butyric Acid is a reactant involved in the synthesis of meta- and paracyclophanes containing unsaturated amino acids and intramolecular Friedel-Crafts reactions for synthesis of 1-tetralones.
Uses
Reactant involved in:• ;Synthesis of meta- and paracyclophanes containing unsaturated amino acids1• ;Intramolecular Friedel-Crafts reactions for synthesis of 1-tetralones2Involved in investigations of pharmacological activity pertaining to:• ;Apoptosis, proliferation, and histon deacetylase activity in human colorectal cancer cells3,4• ;Portable albumin binders for extending the half-life of contrast agents5
Uses
4-(p-Iodophenyl)butyric Acid is a reactant involved in the synthesis of meta- and paracyclophanes containing unsaturated amino acids and intramolecular Friedel-Crafts reactions for synthesis of 1-tetralones.
Synthesis
4-Phenylbutyric acid (20.0 g, 121.8 mmol) was added to a mixed solution of periodate (H5IO6, 5.56 g, 24.4 mmol), iodine (I2, 13.30 g, 52.4 mmol), 10 M sulfuric acid (H2SO4, 5.0 mL), water (36 mL), and acetic acid (166 mL), and the reaction was heated at 70 °C for 19 hours. Upon completion of the reaction, the reaction mixture was cooled and evaporated to dryness. The residue was dissolved in ethyl acetate (EtOAc, 300 mL), washed sequentially with aqueous sodium thiosulfate (Na2S2O3) (2×200 mL) and saturated saline (2×200 mL), dried with anhydrous sodium sulfate (Na2SO4), filtered, and then the solvent was evaporated to give the crude product as a yellow solid. The crude product was recrystallized by ethyl acetate/hexane mixed solvent at 0 °C to afford the target product 4-(p-iodophenyl)butanoic acid as a light yellow solid (15.0 g, 42% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ11.0 (broad single peak, 1H), 7.61 (double peaks, J = 8.4 Hz, 2H), 6.95 (double peaks, J = 8.0 Hz, 2H), 2.63 (triple peak, J = 7.6 Hz, 2H), 2.38 (triple peak, J = 7.6 Hz, 2H).
References
[1] Mendeleev Communications, 2015, vol. 25, # 2, p. 111 - 113
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5919 - 5924
[3] Patent: US2018/66298, 2018, A1. Location in patent: Paragraph 0172; 0173; 0174
[4] Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274
[5] Patent: US2348231, 1940,
