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The Studies On The Properties Of 2, 4-Dimethyl-3-pentanone And Its Deratives

Posted on:2005-12-11Degree:MasterType:Thesis
Country:ChinaCandidate:Z J DuFull Text:PDF
GTID:2121360125450854Subject:Organic Chemistry
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In this thesis were studied influence factors of bromination with 2,4-Dimethyl 3-pentanone. 2,4-Dimethyl 3-pentanone was reacted with bromine at different radio of mole fruction in the presence of PCl3 as catalyst, the selective synthesis of mono or di bromide were obtained. In portant intermediate of food additive 2,2,4,4-tertramethyl –3-sulfcyclobutanone was synthesized by 2,4-dibromo-2,4-Dimethyl 3-pentanone, or bectericidin garic allyl multisulfide was synthesized by allyl bromide. The conjugated compound of α,β-unsturated ketones were obtained. When elimination with mono or dibromide , we were investgate that increasement of three carbon atoms byα,β-conjuated ketones.The silyl enol 9,11 and 13 were prepared by the reaction of TMSCl with ketones. Then silyl enols of 9,11 and 13 progrees to Michael addition with acryl ester, the increasement of three carbon atoms of keto-esters 10,12,14 were affored. This method for sythesis of 10,12 and 14 were unreported.Ⅰ2,4-Dimethyl 3-pentanone react with bromine for different ratio of mole frunction in the presence of and the sythesis of 2,2,4,4-quadrimethyl –3-sulfcyclobutanone PCl3 as catalyst, the mono or dibromide were obtained selectively.1 yield=91% 2 yield=86%⒉The intermediate of food additive-2,2,4,4-tetramethyl –3-sulfancyclobutanone was synthesized and the yield increased 82% from 60%, and the productive technics were simplified greatly.3 yield=82%⒊Refering ⒉, the allyl multislufide aether was synthesized4 yield=81%5ⅡThe elimination reaction of 2-Bromizing-2,4-Dimethyl 3-pentanone and the addition reaction to the elimition production of⒈The effects of different conditions of the elimination reaction were studied and the conclusion was the elimination reaction of halide ketone had better be reacted in organic alkali and polarity solvent, heating. The elimination reaction of dibromide ketone wasn't affected by the quantity of the alkali, the production was 2,4-Dimethyl 1,4-dialkene ketone. 6 yield=54.5%7 yield=71%The compounds 6,7 haven't been found in the literature, and their IR and 1HNMR were tested.⒉Reaction of 2,4-Dimethyl 3-pentanone with methanol or 2,4-Dimethyl 3-pentanone with trimethyl silyl enol pyruvic ethyl ester was studied, and the product was 1,4-additive but was not 1,2 additive product.8 yield=87%9 yield=91% 10 yield=53%The compounds 8,9,10 haven't been found in the literature, and their IR and 1HNMR were tested.ⅢCompound 10 increased three carbon atoms from 9, the study of the Michael addition reaction to 2,4-Dimethyl 3-pentanone and acrylic acid methyl ester⒈The Michael addition reaction to 2,4-Dimethyl 3-pentanone with acrylic acid methyl ester was catalyzed by the ordinary NaOCH3 and NaH, the result was no reaction was found. It might be the alkalinity of NaOCH3 and NaH weren't enough.⒉The Micheal additive reaction to 2,4-Dimethyl 3-pentanone with acrylic acid methyl ester was got by the method of enol sillyl aether, and the production was 3-[2'-(2',4'-2,4 Dimethyl 3'-pentanone)]propionic acid methyl ester. Tthe production wasn't enol sillyl aether.The 4,4,6-trimehtyl-5-carbonylheptanoic acid methylester 12 and 4,4-dimethy-5-carbonyl hexanoic acid methyl ester 14 were obtained by using the Michael addition. 11 yield=95%12 yield=55%The compounds 11 and 12 haven't been found in the literature, and their IR and 1HNMR were tested.13 yield=85%14 yield=57.4% When to proceed the elimination on the methyl isopropyl ketone were afforded the same reault,the compound 12 and 14 weren't enol sillyl aether, the reason might be two methyls and a propionic acid methyl ester group on one side of the carbonyl group of ketone, and might be the conjunct function of the substituting groups on both sides of the carbonyl group. In this paper , 14 compounds had been synthesized, of which, 6,7,8,10,11,12 and 14 haven't been found in the literature, and they were...
Keywords/Search Tags:4-Dimethyl-3-pentanone
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