Experimental Outline: You will receive a vial containing 100 mg of ethyl 3-hydroxybenzoate contaminated with triethylamine. You will also receive four different H NMR spectra: one of the mixture in your vial, and one each of pure ethyl 3-hydroxybenzoate triethy lamil and diethyl ether oEt Ethyl 3-Hydroxybenzoate Triethylamine MP72-74°C Dissolve your sample in 50-75 mL of ether in a separatory funnel Remove the amine by extraction with a 10%o HCl solution Continue with a standard aqueous work-up, including an ether back- extraction-see Extraction and Washing guide. Remove the solvent by rotary evaporation to a constant weight, and obtain a mass Take a H NMR spectrum of the compound and compare to the other spectra Recombine the nmr sample with the remainder of the purified sample Remove the solvent for the final time to a constant weight. Obtain a mass and a melting point. Helpful Hints When removing solvent with the rotary evaporator, make sure the receiving flask is cold and the water bath is warm. otherwise your product will never solidify If you have trouble getting your product to solidify, try adding a few milliliters of methylene chloride to your flask and returning it to the rotary evaporatorExperimental Outline: • You will receive a vial containing 100 mg of ethyl 3-hydroxybenzoate contaminated with triethylamine. You will also receive four different 1 H NMR spectra: one of the mixture in your vial, and one each of pure ethyl 3-hydroxybenzoate, triethylamine, and diethyl ether. O Et HO OEt N Et Et Ethyl 3-Hydroxybenzoate Triethylamine MP 72–74 °C • Dissolve your sample in 50–75 mL of ether in a separatory funnel. • Remove the amine by extraction with a 10% HCl solution. • Continue with a standard aqueous work-up, including an ether back￾extraction - see Extraction and Washing Guide. • Remove the solvent by rotary evaporation to a constant weight, and obtain a mass. • Take a 1 H NMR spectrum of the compound and compare to the other spectra. • Recombine the NMR sample with the remainder of the purified sample. • Remove the solvent for the final time to a constant weight. • Obtain a mass and a melting point. Helpful Hints: • When removing solvent with the rotary evaporator, make sure the receiving flask is cold and the water bath is warm. Otherwise, your product will never solidify. • If you have trouble getting your product to solidify, try adding a few milliliters of methylene chloride to your flask and returning it to the rotary evaporator. 15