2-Heptanone benzylation

Zhao, X., Yu, Z.-Y., Zhou, R., and Eiu, Y. Excess molar enthalpies for binary mixtures of benzyl alcohol and heptanone isomers at different temperatures, J. Chem. Eng. Data, 46(5) 1258-1260, 2001. 

Regioselective alkylation of a methyl ketone Even though the kinetic enolate of 2-heptanone consists of a mixture of terminal and internal enolates in the ratio 87 13, benzylation in DME results in preferential internal alkylation. Regioselective benzylation at the terminal position can be enhanced by addition of various ligands such as benzo-14-crown-4 and DMF, but HMPT is the most effective ligand, resulting in a ratio of terminal to internal benzylation of 11 1. The three ligands also increase the rate of alkylation. The same effect, but less marked, is observed in alkylation with the less reactive electrophile butyl iodide. 

Ifenprodil (= l-Methyl-2-hydroxy-2-(4-hydroxyphenyl) ethyl-1 -(4-benzyl-piperidine)] -(aryl piperidine) [at(/o-3-(Indol-2-yl)-8-methyl-8-azabicyclo-[3.2.1] octane] (indolotropane) [Kynurenic acid (= 4-Hydroxy-2-quinolinecarboxylic acid)] (quinoline carboxylic acid) [Memantine (= 1-Amino-3,5 dimethyladamantane)] (amino adamantane, amino cyclic aliphatic) [Methadone (= 6-Dimethylamino-4,4-diphenyl-3-heptanone)] (aryl tertiary amine) [em/o-3-(l -Methylindol-2-yl)-8-methyl-8-azabicyclo-[3.2.1] octane(indolotropane) exo- 3-( 1 -Methylindol-2-yl)-8-methyl-8-... 

Other olefinic ketones have been reduced selectively at room temperature and atmospheric pressure over a platinum or palladium catalyst to give good yields of the ketones, namely, 5-methyl->heptanone (94%), diisobutyl ketone (100%), and a-benzylacetophenone (81-95%). Selective hydrogenations of some 3-alkyl-2-cyclohexenones have been carried out over palladinized charcoal in essentially quantitative yields. Preparation of platinum catalyst has been described. Many olefinic ketones prepared by the aldol condensation or by acylation of olefins have been hydrogenated however, the yields are not always stated. Benzalacetone, CgHsCHasCHCOCHj, is selectively reduced to benzyl-acetone in a 63% yield by the action of sodium amalgam in acetic acid-alcohol solution. ... 

Synonyms 1-Benzyl dipropyl ketone 3-Benzyl-4-heptanone 4-Heptanone, 3-benzyl- 4-Heptanone, 3-(phenylmethyl)- Morellone Empirical C14H20O Properties Liq. m.w. 204.34 Toxicology LD50 (oral, rat) 4400 mg/kg low toxicity by ing. 

Heptan-4-one. See 4-Heptanone 4-Heptanone, 3-benzyl-. See Benzyl dipropyl ketone... 

Potato Methional,2,3-Dimethylpyrazi ne Prtme Benzyl-4-heptanone, Dimethylbenzylcarbiny lisobutyrate... 

Tian et al. showed later that other ketones can be apphed in the reaction [74] when benzyl(triphenyl)phosphonium chloride was used as the phosphonium salt based catalyst The desired product was obtained in 92% yield in the reaction of 2-heptanone with TMSCN in 24h (Scheme 16.27). The authors pointed out that it was essential to apply the chloride salt in the reaction. When a bromide analog was used, a very low yield of 2.6% was observed. 

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