Image from page 19 of "Correlation of ionization and structure" (1912)
Title: Correlation of ionization and structure
Year: 1912 (1910s)
Authors: Hollman, Edward Emil
Subjects: Ionization Chemical structure Ionization constants Theses
Contributing Library: University of Illinois Urbana-Champaign
Digitizing Sponsor: University of Illinois Urbana-Champaign
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aration of Allyl Acetic Acid and Its Sodium Salt. The problem was to prepare as pure a product as possible,and to this extent the intermediate products formed were purifiedwherever it 7;as deemed expedient,I. Allyl Bromide:- PBr3 was dropped into allyl alcohol. The action v/as vigor-ous but could be easily controlled. The whole was then refluxedfor fifteen minutes to complete the reaction,and treated withNaa.C03 to destroy the HBr dissolved in the mixture. Yield:- 73^,B.P.(allyl bromide):- 70,3C.Malonic Acid Synthesis:- II. Allyl Malonic Ester:-The calculated amount of allyl bromide was added slowly thru a reflux condener to a freshly prepared,alcoholic solution ofsodium malonic ester. The action v;as very vigorous and a whiteprecipitate of NaBr separated out. The whole was refluxed foron© and one-half hours. The reformed alcohol was then distilledoff,and the ester distilled over between 210-228*C. III. Allyl Malonic Acid:-The allyl malonic ester obtained above r/as saponified with |
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twice the theoretical amount of KOII (1.25^x8.KOII in iigra.HiO).TtLO saponification was coniplete aftor boiling for three hours aawas shown by an otiier extraction. On evaporation of the etherno residue oil was left. The yellow solution of the potassiumsalt of allyl malonic acid was then carefully neutralized withconcentrated hydrochloric acid, A white precipitate foriuedbut this was found to be potassium chloride and was filtered off.To the filtrate was then added a cold saturated solution of cal-cium chloride until no more precipitate formed on hsatinr; a fil-tered portion. This calcium salt was then filtered off andpressed dry,moistened with a little water,and the free acid ob-tained by adding concentrated hydrochloric acid until the wholewas in solution. The free acid was then extracted with ether.On evaporation of the ether in a vacuum dessicator the allylmalonic acid was obtained as a white,crystalline product. Asmall amount of mother liquor was left;this was filtered off,press
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