Methyl-0-naphthyl ether, formation

Formation of Methyl- -Naphthyl Ether. In a test tube provided with reflux micro-condenser place 0.5 g of /3-naphthol, 2 ml of 10 per cent sodium hydroxide solution, and 0.5 ml of methyl iodide. Warm for 20 minutes in a water bath, and then note the odor. Add 5 ml of water and filter the crystals, washing with water. The ether may be recrystallized from alcohol. 

Alongside ester condensations ranks a series of simple condensations that involve formation of a new carbon-carbon bond with loss of an alcohol but that can be applied only in isolated cases. One such is the condensation of acetals with aromatic compounds with loss of alcohol, as when ethyl diethoxy-acetate and nerolin (methyl 1-naphthyl ether) in glacial acetic plus sulfuric... 

To prevent the formation of abnormal Claisen product, Kishi et al. demonstrated trapping the resulting phenolic hydroxyl group by acetylation by carrying out the reaction in acetic anhydride in the presence of potassium or sodium acetate under thermal conditions [42]. For example, 3-methyl-2-butenyl 1-naphthyl ether 44 was... 

Chelation-assisted C-H/olefin coupling can be applied to the atroposelective alkylation of biaryl compounds. The reaction of 2-(l-naphthyl)-3-methylpyri-dine with ethylene using [RhCl(coe)2]2 where coe is cyclooctene, and PCy3 results in the formation of an ethylation product in 92% yield (Eq. 21) [20]. In place of the PCy3 ligand, the use of (R) - (1 - [ (S) - 2- diphenylphosphino ] ferro-cenyl)ethyl methyl ether [(R),(S)-PPFOMe] leads to the atropselective alkyla-... 

Maltol Isobutyrate 2-Methoxy 3-(or 5- or 6-) Isopropyl Pyrazine 5H-5-Methyl-6,7 -dihydrocyclopenta[b]pyrazine 5-Methyl Furfural Methyl Furoate Methyl Hexanoate Methyl Isovalerate 5-Methyl 2-Phenyl 2-Hexenal Methyl Thiobutyrate Methyl Valerate P-Naphthyl Ethyl Ether Phenyl Ethyl Cinnamate Phenyl Ethyl Propionate Propyl Formate Propyl Mercaptan Salicylaldehyde 8-T etradecalactone 2-Tridecanone... 

Di-(l-naphthylmethyl)sulphone forms an excimer but does not react to give an intramolecular cycloaddition product like the corresponding ether but rather fragments to give sulphur dioxide and (l-naphthyl)methyl radicals (Amiri and Mellor, 1978). I-Naphthylacetyl chloride has a very low quantum yield of fluorescence and this is possibly due to exciplex formation between the acyl group and the naphthalene nucleus (Tamaki, 1979). Irradiation leads to decarbonylation. It is known that acyl chlorides quench the fluorescence of aromatic hydrocarbons and that this process leads to acylation of the aromatic hydrocarbon (Tamaki, 1978a). The decarboxylation of anhydrides of phenylacetic acids [171] has been interpreted as shown in (53), involving... 

Alonsono and co-workers [146] have used substituted 1-naphthyl and phe-nylphosphonium chlorides as precursors for the generation of the corresponding arylmethyl radicals and cations in both nanosecond LFP and product studies. For instance, the salt 101 has a quantum yield for cation formation of 0.71 in methanol and the sole product observed was the corresponding methyl ether. No transient radical was observed in this solvent. In contrast, in 5% acetonitrile in dioxane, the radical was observed but now the cation was absent. No fluorescence was observed in either solvent suggesting that Si is very reactive. Redox potentials indicate that the conversion of the radical/radical ion pair to the cation/triphenyl-phosphine pair would be exothermic by some 25 kcal/mol. Therefore, both heterolytic cleavage from Si or homolytic cleavage followed by electron transfer were suggested as possible pathways for cation formation. 

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... 

Methyl propionate 3-Methyl-5-propyl-2-cyclohexen-1-one Methyl propyl ketone Methyl tiglate Methyl p-toluate Methylundecanal dimethyl acetal Methyl 9-undecenoate Methyl 10-undecenoate Methyl valerate Methyl vanillate Musk ketone Musktibetene Myrcene Myrcenol Myrcenyl acetate Myristaldehyde Myrrh gum Myrtenol Myrtenyl acetate Myrtenyl formate Myrtle (Myrtus communis) extract Myrtle (Myrtus communis) oii P-Naphthyi isobutyl ether P-Naphthyl methyl ether Neral Nerol Neryl acetate Neryl butyrate Neryl formate Neryl isobutyrate Neryi isovaierate Neryi propionate Nona-2,4-dienai trans,trans-2,4-Nonadienal 2,6-Nonadien-1-ol... 

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). 

Methyl 8-benzhydryl-l-naphthoate added to excess methyllithium prepared from methyl iodide and lithium in ether, and the product isolated after 5 hrs. refluxing methyl 8-benzhydryl-l-naphthyl ketone. Y 92%.—A second mole of methyllithium enolizes the ketone with formation of methane, a general type of reaction of hindered alkyl ketones. Phenyllithium yields a tert. carbinol since enolization of the intermediate is not possible. R. L. Letsinger and P. T. Lans-bury, Am. Soc. 81, 935 (1959). 

Prandi and coworkers investigated cychzation reactions involving dien-amides they found differential reactivity based on the substitution pattern of the dienamide (Scheme 48 2011OBC2535). For example, treatment of dienamide 211 with TFA led to the formation of 3-pyrrolin-2-one 212. The same reaction with the methyl-containing substrate 213 led to the formation ofimino ether 214. The structures of the 3-pyrrolin-2-one products were confirmed by ROESY NMR experiments the structure of one of the imino ether products (N-naphthyl) was confirmed by single crystal X-ray analysis. 

Analogous ring expansion via P-fragmentation of cyclobutanoxyl radicals derived from the photoadducts between a- or P-naphthyl trimethylsilyl ether and acrylonitrile or methyl acrylate resulted in the formation of a benzohomotropone after treatment with a base. 

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