Ethyl-2-naphthyl ketone

Obtained from sodium-liquid ammonia reduction of 4,6-dimethoxy-l-naphthyl ethyl ketone in THF/EtOH mixture in presence of excess ammonium chloride [7851]. pale yellow oil [7851 ] b.p. 80° [7851 ] ... 

In fact, the reaction proceeded as expected [23]. Thus, by heating the l-[o-(l-alkynyl)phenyl]cyclopropanol complexes 36-Co2(CO)6 in refluxing 2-propanol, 2,3-dihydro-1-naphthalenone derivatives 37 are obtained as a mixture of (Aland (Z)-isomers in moderate yield accompanied by a substantial amount of an ethyl ketone derivative formed by ring opening of the cyclopropanol moiety. Furthermore, when an analogous naphthyl derivative 38 was employed, the reaction proceeded cleanly and the 2,3-dihydrophenanthren-l-one derivative 39 was obtained in 83 % yield (Scheme 17). The obvious difference in reactivity between phenyl and naphthyl derivatives is probably due to the presence of hydrogen at the peri position of the latter. To avoid steric repulsion between the alkyne-Co2(CO)6 moiety and this hydrogen, the molecule adopts a conforma-... 

Hexen 3,5-Dioxo-l-phenyl- El 9b, 1261 (Hydroxy-carben - Keton) Flydroperoxid l-(2-Naphthyl)-ethyl-E13/1, 161 (O-Ac - O-OH) Inden... 

Methyl-1-propanethiol Methyl propionate 3-Methyl-5-propyl-2-cyclohexen-1 -one Methyl propyl ketone 2-Methylpyrazine flavoring agent, synthetic food Methyl salicylate Methyl sorbate 5-Methyl-2-thiophenecarboxyaldehyde 3-Methylthiopropionaldehyde 2-Methyl-3-tolylpropionaldehyde, mixed o-, m-, p-Methyl 9-undecenoate Methyl 2-undecynoate Methyl valerate MSG Musk ambrette Myrcene Myristaldehyde Myristyl alcohol Myrtenol 2-Naphthalenethiol P-Naphthyl ethyl ether P-Naphthyl isobutyl ether d-Neomenthol Nerol Neryl acetate Neryl butyrate Neryl formate Neryl isobutyrate Neryl isovalerate Neryl propionate... 

In a completely analogous manner, the methoxy acid (326 R = MeO) was synthesized from the ketone (324 R = MeO). In this case the starting material was obtained from /3-(6-methoxy-l-naphthyl)ethyl bromide (3) (Scheme 1) by treatment with potassium cyanide and hydrolysis to naph-thylpropionic acid and the reaction of the chloride of this acid with dime thy Icadmium, leading to the methoxyketone (324 R = MeO) [417]. 

An attractive alternative to these novel aminoalcohol type modifiers is the use of 1-(1-naphthyl)ethylamine (NEA, Fig. 5) and derivatives thereof as chiral modifiers [45-47]. Trace quantities of (R)- or (S)-l-(l-naphthyl)ethylamine induce up to 82% ee in the hydrogenation of ethyl pyruvate over Pt/alumina. Note that naphthylethylamine is only a precursor of the actual modifier, which is formed in situ by reductive alkylation of NEA with the reactant ethyl pyruvate. This transformation (Fig. 5), which proceeds via imine formation and subsequent reduction of the C=N bond, is highly diastereoselective (d.e. >95%). Reductive alkylation of NEA with different aldehydes or ketones provides easy access to a variety of related modifiers [47]. The enantioselection occurring with the modifiers derived from NEA could be rationalized with the same strategy of molecular modelling as demonstrated for the Pt-cinchona system. 

Strawberry Anisyl formate benzyl isobuiyrate Cuminic alcohol Ethyl methylphenylglycidaie Ethyl phenylglycidate Isoamyl salicylate Isobuiyl anthranilate Meihylacetophenone Methyl cinnamate. Methyl naphthyl ketone Nerolin Neryl isobutyrate Phenylglycidate... 

Other hemiacetals which have been prepared include the methyl 8<9a>, ethyl 9b), and isopropyl hemiacetals 81) of tetramethylcyclopropanone, the phenyl, a- and (3-naphthyl hemiacetals of cyclopropanone 82>, and the benzyl hemiacetal of 2,3-di-f-butylcyclopropanone. 13> In the last case, the benzylic methylene protons display an AB pattern in the PMR spectrum indicating that the two Ybutyl groups are trans to one another. Although derivatization of this di-f-butyl ketone was possible, carbonyl addition may be hindered by steric factors as suggested by the lack of reaction of 2,2-diY-butylcyclopropanone with methanol. 55a>... 

Magnesium, 12, 48 Malononitrile, 10, 66 Malonylurea, see Barbituric acid Mercuration, 12, 46, 54 Mercuric chloride, 12, 54 Mercuric oxide, 12, 44 Mercury di-/3-naphthyl, 12, 46 Mesaconic acid, 11, 74 Mcsitylene, 11, 24, 67 Methylamine, 12, 38 Methylamine hydrochloride, 10, 112 Methyl -amyI ketone, 10, 60 M ethylation of thiourea, 12, 52 Methyl benzoate, 10, 51 Methyl chloride, 10, 32, 36 Methylene bromide, 10, 112... 

Acetylation of naphthalene gives methyl naphthyl ketone, and sulfonation followed by alkaline fusion gives naphthol (Scheme 4.60). The methyl and ethyl ethers of naphthol are prepared from naphthol by reaction with the corresponding alkyl sulfate under basic conditions. These ethers are usually known by the shorter names of yara and nerolin, respectively. Yara, nerolin and methyl naphthyl ketone possess floral odours and are moderately important perfume ingredients. 

Naphthyl substituent shows a different character in the excited state in comparison with phenyl substituent. The photohydration of 1-phenyl-5,5-dim-ethyl-l,3-hexadiyne gives three photohydration products (58-60) (two acetylenyl ketone and one allenyl ketone) through both Si and Tj excited states (Scheme 20). An allenyl ketone product is obtained as a minor product. A proposed mechanism involves the protonation step as the rate limiting step in the formation of acetylenyl ketone products. On the other hand, the allenyl ketone product is formed by the synchronous addition mechanism of H3O+. 

Dimethyl sulfide N,N -Di-P-naphthyl-p-phenylenediamine 2,4-Dinitrophenyl phenyl sulfide Ethyl-N-butylamine 2-Ethylhexanal 2-Ethylhexenal 2-Ethyl-2-hexenal Ethyl vinyl ketone Formamide Glyceryl-a-monochlorohydrin... 

Because a different stereochemistry for the aza-MBH reaction involving different Michael acceptors was observed, in a continuation of our work, we reinvestigated systematically the reaction of iV-sulfonated imines with various activated olefins, including ethyl vinyl ketone (EVK), acrolein, phenyl acrylate and a-naphthyl acrylate. An interesting inversion of absolute configuration between the adducts derived from MVK or EVK and those from acrolein, methyl acrylate, phenyl acrylate or a-naphthyl acrylate was observed, indicating that the substitution patterns of the olefin may alter or even invert this trend.Similar to the addition to HFIPA, the (3-ICD-mediated addition of methyl, phenyl and naphthyl acrylates 149 to V-sulfonyl imines afforded adducts 150 with an (5) configuration, which is opposite to that observed with aldehydes (Scheme 2.71). ... 

A soln. of crude methyl 1-naphthyl ketone and ethyl formate in dry ether added slowly with shaking to Na-wire in dry ether, and refluxed 4 hrs. perinaphthe-none (Y 64%) in dioxane hydrogenated 8 hrs. at 260° with copper chromite at an initial Ha pressure of 120 atm. in a glass-lined autoclave perinaphthane (Y 80%). — The amount of Gu-chromite is critical. I. K. Lewis and R. D. Top-som, Australian J. Ghem. 18, 923 (1965). 

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