α-Chloro- and α-iodoacetylsalicylic acids reacted differently with certain reagents.Mechanisms were proposed to account for these differences.Equimolar amounts of 1,2-AcOC6H4COCl and Et2NCH2CH2OH in refluxing Et2O gave 10% 1,2-AcOC6H4CO2CH2CH2NEt2, m. 136.5-7.5°.1,2-ClCH2CO2C6H4CO2H (I) and a small amount of Cu in absolute EtOH at -20° with NH3 gas gave 77.7% ClCH2CONH2 and 76.5% 1,2-HOC6H4CO2H.I in Et2O at 0° with NH3 gave 83% 1,2-ClCH2CO2C6H4CO2NH4, m. 70-2°, which had been reported erroneously to be 1,2-HOC6H4O2CCH2NH2.HCl (Kaufmann and Thomas, C.A. 18, 3051).The NH4 salt structure was based on the recovery of 91-8% I after treatment with dilute HCl.1,2-ClCH2CO2C6H4CO2Me (II) was treated with an equimolar amount of NaI in acetone to give a precipitate of NaCl, which was filtered off.Pyrrolidine (III) was added to the filtrate at 5-15° and worked up to give 20% 1,2-(CH2)4NHCH2CO2C6H4CO2Me.Cl (IV), m. 131-2°.Another exp. gave a polymorphic form of IV, m. 146-7°.1,2-Et3NCH2CO2C6H4CO2CH2Ph.I, m. 101-3°, was prepared in 38% yield by a similar procedure.I by a similar process with III gave 64% rearranged product, 1,2-(CH2)4NCOCH2O2CC6H4OH (V), m. 131-2°, and I with morpholine gave 1,2-O(CH2CH2)2NCOCH2O2CC6H5OH.I with Et3N treated similarly gave an intermediate, 1,2-O.CO.C6H4.CO.O.CH2 (VI), m. 115-15.5°.VI with III gave V.VI with H2O gave 1,2-HOC6H4CO2CH2CO2H, m. 132°.As proof of structure, V was also prepared in 60% yield from 1,2-HOC6H4CO2Na and (CH2)4NCOCH2Cl (VII).PhCH2O2CNHCH2CH2CO2H and 1,2-HOC6H4CO2H (VIII) in Et2O with C5H5N gave 1,2-PhCH2O2CNHCH2CH2CO2C6H4CO2H (IX), m. 121-2°.IX with Pd-C in MeOH was hydrogenated to H2NCH2CH2CO2Me and VIII.When I was treated directly with III without going through the intermediate iodo compound, VII and VIII were formed.AcOC6H4CO2H with EtOH and Et3N gave AcOEt and HOC6H4CO2NEt3.HI.IR absorption data for many of the compounds were given.