It was shown that the decarboxylative acylation of carboxylic acids having a suitable electron-attracting group in the α-position is a base-catalyzed condensation of an anhydride with the C:O group of the acylating agent.The scope and stoichiometry of the reaction have been further defined.Probable reaction sequences for the various acids undergoing the reaction are discussed.Me2C(NH2)CO2H (10.3 g.), 102. g. Ac2O, and 79 g. pyridine refluxed 6.5 hrs. and then distilled gave 4 fractions, b. 113-24°, 125-30°, 130-4°, and 134-8°, resp.CCl3CO2H (16.3 g.), 100 cc. Ac2O, and 100 cc. pyridine refluxed 2.5 hrs., the mixture distilled to 113°, the distillate extracted with three 10-cc. portions CH2Cl2, and the extract dried and fractionated gave 3.5 g. CHCl3, b. 56-60°, nD25 1.4403; the original pot residue neutralized with aqueous NaHCO3 and extracted with three 250-cc. portions CHCl3, and the extract dried and distilled gave no material boiling above 115° and left a negligible tarry residue.PhCH(NH2)CO2H (15.1 g.) and 100 cc. Ac2O refluxed 0.5 hr. and fractionated gave 3.0 g. distillate, b13 135-44°, and 3.2 g. distillate, b0.25 130-40°; the 1st fraction redistilled gave 1.5 g. 2,5-dimethyl-4-phenyloxazole, b0.2 68-84°, nD25 1.5500; HCl salt, m. 159-60° (from EtOH); picrate, m. 130-1° (from 95% EtOH); the higher boiling, more viscous fraction was AcNHCHPhAc, m. 98.5-9.5°.N-Benzoyl-DL-alanine (I) (19.3 g.), 100 cc. Ac2O, and 100 cc. pyridine refluxed until the CO2 evolution ceased, the excess reagents distilled off, and the pot residue recrystallized from CCl4-Skellysolve B gave 16.1 g. BzNHCHMeAc (II), m. 69-70°.I (19.3 g.), 20.4 g. Ac2O, and 100 cc. pyridine refluxed 40 min. (2040 cc. CO2 was evolved), the mixture distilled at 40 cc. from a bath below 120°, the head, condenser, and receiver rinsed with pyridine, the combined rinsings and distillate treated with 18.0 g. PhNH2, the mixture evaporated in vacuo on the steam bath, and the residue treated with 50 cc. H2O, acidified with HCl, and chilled gave 12.9 g. PhNHAc, m. 108-9°; the pot residue distilled gave 18.1 g. II, b0.15 105-16°, which crystallized in the receiver.I was converted by the method of Mohr and Stroschein (C.A. 3, 2579) to 84% 2-phenyl-4-methyl-oxazolin-5-one (III), b0.2 90-2°, nD25 1.5486.III (18.8 g.), 3.0 g. AcOH, and 50 cc. pyridine refluxed 2 hrs. and the mixture fractionated gave 9.2 g. II, b0.2 110-17°, and a lower boiling fraction, b35-40 up to 60°; the 1st fraction treated with 5.4 g. PhNH2, the mixture evaporated on the steam bath in vacuo, and the residue treated with dilute HCl and chilled gave 1.98 g. PhNHAc, m. 108-10°.The same amounts III, AcOH, and pyridine refluxed 1.5 hrs. with 5.2 g. Ac2O, and the product worked up with 10.24 g. PhNH2 gave 5.78 g. PhNHAc, m. 108-11°, and 9.2 g. II b0.2-0.3 123-5°.III (8.8 g.), 3.00 cc. AcOH, and 50 cc. pyridine refluxed 3 hrs. (760 cc. CO2 was evolved) and the mixture fractionated gave a small amount BzOH, m. 118-19°, and 7.1 g. II, b0.1-0.2 119-25°, m. 62-4.5°.PhCH2(Me)NCH2CO2H (17.9 g.), 100 cc. Ac2O, and 100 cc. pyridine refluxed about 5 hrs. until the CO2 evolution ceased (2400 cc. CO2 was evolved), and the mixture distilled gave 14.5 g. distillate, b0.4-0.5 114-21°, which fractionated yielded 3 fractions: 2.2 g., b0.1 97-9°; 7.8 g. b0.1 97-9°; and 1.0 g., b0.1 99-105°; the 2nd fraction, m. 42.5-44°, was AcNMeCH2Ph.In a similar run the reaction mixture fractionated at. atm. pressure could not be distilled up to 113°; Me2CO was thus not formed in the reaction.