Ethyl-2-naphthyl ether

A. Reduction and hydrolysis. A solution of 129 g. (0.75 mole) of 0-naphthyl ethyl ether in 1.5 1. of 95% ethanol is prepared in a 5-1. three-necked flask fitted with a mechanical stirrer, a bulb condenser topped by a Friedrichs condenser, and a Y-tube to allow for the introduction of nitrogen and sodium. The apparatus is llushed thoroughly with nitrogen, the nitrogen flow is reduced, and 225 g. (9.8 gram atoms) of sodium is added in small portions (Note 1), wilh efficient stirring, at a rate suffi-... 

Naphthalenolsulfonic acid formaldehyde condensates are used in tanning agents. Other uses of 2-naphthalenol are in the manufacture of perfuming agents, eg, 2-naphthyl methyl e e [93-04-9] (Yara Yara), R = CH (30), and 2-naphthyl ethyl ether/Pi-/ -37 (nerolin, BromeUa) R = ... 

Naphthol, 18 /3-Naphthyl ethyl ether, 11 Nef reaction, 40 Nichrome helices, 96 Nitrobenzene, 1 5-Nitroindazole, 73 /i-Nitrophenol, 60 NON AMETHYLENE BROMIDE, 25... 

With liquid or low-melting ethers no solvent is required. 2-Ethoxy-i-naphthaldehyde has also been prepared by ethylation of the hydroxy compound,11 and from /3-naphthyl ethyl ether by the Gattermann reaction.12... 

B. Bisulfite addition product of /3-tetralone. To a solution of 325 g. (3.12 moles) of sodium bisulfite (commercial purified grade) in 565 ml. of water is added 175 ml. of 95% ethanol. The mixture is allowed to stand overnight, and the precipitated sodium bisulfite is removed by filtration. The filtrate is added to the crude /3-tetralone, and the mixture is shaken vigorously. Within a few minutes the addition product separates as a voluminous precipitate. The mixture is kept cold for several hours, shaken periodically, and then filtered with the aid of suction. The precipitate is washed well, first with 125 ml. of 95% ethanol, then four times with 125-ml. portions of ether (Note 6). The colorless addition product is air-dried (Note 5) and is stored in air-tight containers. The yield is 113-131 g. (60-70% based on /3-naphthyl ethyl ether) (Note 7). 

C. Regeneration of 0-tetralone. Fifty grams (0.20 mole) of /3-tetralone bisulfite addition product is suspended in 250 ml. of water, and 75 g. (0.6 mole) of sodium carbonate monohydrate is added. At this point the pH of the solution is approximately 10. The mixture is extracted with five 100-ml. portions of ether (Note 8). The combined extract is washed with 100 ml. of 10% hydrochloric acid, then with 100-ml. portions of water until the washings are neutral to litmus, and is dried over anhydrous magnesium sulfate. The ether is removed by distillation, and the residue is distilled from a Claisen flask under reduced pressure, preferably in a nitrogen atmosphere. The pure /3-tetralone is obtained as a colorless distillate b.p. 70-71°/0.25 mm. (92-940/1.8 mm., 114-11674.5 mm.) n 1.5594. The yield is 17-21 g. (40-50% based on /3-naphthyl ethyl ether). 

De Schryver and co-workers u> have confirmed Chandross result for the UV absorbance of l,3-bis(2-naphthyl)propane. Nishijima et al.12) have stated that the absorbance spectrum of meso- and dl-2,4-bis(2-naphthyl)pentane and of the compounds l,3-bis(2-naphthyl)A, where A = propane, butane, pentadecane, and 5-phenylpentane, is similar to the absorbance spectrum of 2-ethylnaphthalene. Finally, an unusual result has been obtained by De Schryver et al.13> for the compound bis(l-(2-naphthyl)ethyl)ether. The meso compound gave a lower value of ID/IM, the ratio of excimer to monomer fluorescence intensities, under excitation at 304 nm relative to excitation at 285 nm, while the dl compound had no such excitation dependence. The UV absorbance spectra of these compounds were not reported, however. 

While the photodimerization of bis(l-naphthylmethyl) ether was acknowledged somewhat earlier 39), the photodimers were first characterized and the quantum yield of the dimerization determined by Todesco et al. U2). Both the syn- and anti-photodimers were formed in roughly equal amounts, and the quantum yield for formation of the anti-dimer was independent of solvent. However, the quantum yields for formation of the syn-dimer and for excimer fluorescence were found to vary with solvent such that their sum was independent of solvent. The fact that irradiation of l,3-bis(l-naphthyl)-1-propanol yields only the syn-photodimer 113> indicates that the conformational properties of oxygen are largely responsible for anii-dimerization in the ether compound. The possibility of photodimerization was unfortunately not considered in the fluorescence studies of protonated bis (1-naphthylmethyl) amine 115>, l,3-bis(4-methoxy-l-naphthyl) propane 116>, and meso-bis( 1 -(1 -naphthyl-ethyl) ether 13). 

Naphthylacetamide, 32, 94 a-Naphthylcyanamide, 31, 20 -Naphthyl ethyl ether, 32, 97 -Naphthyl methyl ether, 32, 100 Neophyl chloride, 32, 90 Nicotinamide, 30, 3 Nicotinonitrile, 1,2-dihydro-... 

The first study of a nucleophilic aromatic substitution in which formation of a Meisenheimer-type complex and its subsequent decomposition were separately observable was reported by Orvik and Bunnett (1970). The study involved the reaction of 2,4-dinitro-l-naphthyl ethyl ether [7] with n-butyl- and t-butylamine in DMSO. The use of DMSO in this kinetic study enabled the rate behaviour to be unambiguously interpreted by avoiding complications due to aggregation phenomena, while stabilizing any a-complexes which are formed. The reaction sequence is given in equation (28). In this OEt... 

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