Acetone → Methyl Benzoate
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Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8](CCN)=[CH:7][CH:6]=1.CC(C)=O.N1C=CC=CC=1.C(OC1C=CC(Cl)=CC=1C(Cl)=O)C>O1CCOCC1>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8](CCN)=[CH:7][CH:6]=1.CC(C)=O.N1C=CC=CC=1.C(OC1C=CC(Cl)=CC=1C(Cl)=O)C>O1CCOCC1>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=110.5 g of 4-(2-aminoethyl)-benzoic acid methyl ester-hydrochloride were suspended in 40 ml of dioxane and 20 ml of acetone and the suspension was combined with 8 ml of pyridine. To this suspension, a solution of 10 g of 2-ethoxy-5-chloro-benzoyl chloride in a small amount of acetone was added dropwise, while stirring, and the whole was heated for 2 hours under reflux. After cooling, the mixture was concentrated under reduced pressure, combined with ice-water, filtered with suction, stirred with dilute hydrochloric acid and with a NaHCO3 solution and the resulting product was again filtered off with suction and recrystallized from ethanol. The 4-(2-<2-ethoxy-5-chloro-benzamido>-ethyl)-benzoic acid methyl ester obtained was found to melt at 110° C.
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