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2 protocols using p toluic acid

1

Purification and Characterization of Organic Compounds

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All deionized water was obtained from a Milli-Q2 system and exhibited a specific resistance of at least 18 MΩ cm. Methanol (99.8%) and 1-pentanol (≥99%) were obtained from Sigma-Aldrich (Milwaukee, WI), as were tetraoctylammonium bromide (TOABr) (98%), tetraoctylammonium chloride (TOACl) (≥97%), menthol (99%), and decanoic acid (98%). All were employed without further purification. Concentrated hydrochloric acid (Optima™ grade), acetone (Optima™ grade), 1-propanol (HPLC grade), 1-butanol (HPLC grade), and hexane (HPLC grade), were purchased from Fisher Scientific (Pittsburgh, PA), while standard (0.100 N) sodium hydroxide solution was obtained from Ricca Chemical Company (Batesville, IN). Ethanol (≥99.5%) was purchased from Decon Labs Inc. (King of Prussia, PA). For liquid scintillation counting (LSC), Ultima Gold™ (Perkin Elmer Corp., Waltham, MA) LS cocktail was employed.
With the exception of phenol (Moravek Biochemicals, Brea, CA) and toluene (American Radiolabeled Chemicals, St. Louis, MO), all 14C-labeled reagents (aniline, benzoic acid, chlorobenzene, phthalic acid, p-toluic acid, and salicylic acid) were obtained from Sigma-Aldrich.
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2

Synthesis and Characterization of Benzyl and tert-Butyl Isocyanides

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Benzaldehyde (≥99%), levulinic acid (98%), p-toluic acid (98%), tert-butyl isocyanide (98%) and trifluoroacetic acid (99%) were purchased from Sigma-Aldrich. Benzyl isocyanide (98%) and 2,2,2-trifluoroethanol (99.8%) were purchased from Acros Organics. 1,1,3,3-tetramethylbutyl isocyanide and ammonia solution (28–30%) were purchased from Merck KGaA. Acetic acid (~100%) was purchased from AnalaR. Methanol (HPLC grade) was purchased from Fisher.
Reactions were carried out using a CEM Discover microwave synthesis unit.
1H–NMR and 13C–NMR spectra were obtained using a Bruker DRX 400 MHz spectrometer. Mass spectrometry was performed on an Agilent Technologies 6520 Accurate-Mass Q-TOF LC/MS connected to an Agilent Technologies1200 HPLC system with UV detector and autosampler.
Radio-HPLC analysis was performed on an Agilent Technologies 1200 Series with UV detector (254 nm) and Lablogic β + radio-detector using an Agilent Eclipse XDB-C18 column (5 μm, 4.6 × 150 mm). The following mobile phase conditions were used: solvent A: H2O + 0.1% TFA; solvent B: MeOH +0.1% TFA; time:%B 0:5, 1:5, 10:95, 18:5, 23:5. Flow rate was 1 mL/min.
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