2-Naphthol methyl ether

However, oxidation of 2-naphthol methyl ether (nerolin) leads to a quinone, namely, 4-(2 -methoxy-l -naphthyl)-1,2-naphthoquinone. 

Naphthol methyl ether P-Naphthol methyl ether. See p-Naphthyl methyl ether... 

Naphthol methyl ether p-Naphthol methyl ether 2-Naphthyl methyl ether Nerolin old Yara yara... 

Synthesis of racemic naproxene Friedel-Crafts acylation (aluminum chloride - nitrobenzene) of p-naphthol methyl ether affords 2-acetyl-6-methoxy naphthalene, which, when treated with either dimethyl sulfonium or dimethylsulfoxonium methylide, gives 2-(6-methoxynaphthalen-2-yl)propylene oxide. Treatment of the latter with boron trifluoride etherate in tetrahydrofuran gives 2-(6-methoxynaphthalen-2-yl)propionaldehyde, which is oxidized using Jones reagent (4 M chromic acid) to yield the racemic 2-(6-methoxynaphthalen-2-yl)propionic acid. 

This synthesis was first carried out by Velluz, Angew, Chem , i960, 72, 725. The lactone can be used instead of the y-chloro acid, see Org. Synth. Coll., 4, 898, Other approaches to A are outlined in J. Amer. Chem. Soc., 19 7> 6.9 > 576, 2936 and it is probable that the reaction actually given here - the cyclisation of B - would give a five membered ring instead (J. Chem. Soc., 1956, 4647) The usual, if illogical way to make A is by reduction of p naphthol methyl ether and oxidation of the product with CrO. ... 

Whereas /3-naphthol methyl ether is oxidized with ring fission by perbenzoic acid in benzene and by peracetic acid in acetic acid at room temperature, it is attacked by perphthalic acid in ether to only a negligible extent. ... 

H. Fernholz studied the oxidation of /8-naphthol methyl ether with perbenzoic acid and presented convincing evidence of the course of a remarkable reaction conversion into the monomethyl ester of o-carboxyallocinnamic acid (6) in 35% yield. Six grams of the ether (1) was added with cooling to 692 ml. of a 2.5% solution... 

P-naphthyl methyl ether, ((i-naphthol methyl ether 2-methoxynaphthalene methyl naphthyl ether). C10H7OCH3. 

AI3-21213 EINECS 202-213-6 P-Melhoxynaphihalene Methyl p-naphthyl ether Methyl 2-naphthyl ether Naphthalene, 2-methoxy- p-Naphthol methyl ether p-Naphthyl methyl ether 2-Naphthyl methyl ether Nerolin NSC 4171 Yara-Yara Yura Yara. Used in perfumery. Leaflets mp = 73.5" bp = 274" djfin 1.0640 Xm = 227,... 

Oxidative removal of hydrogen has been satisfactory more frequently with phenols and their ethers examples are the conversion of 6-methyl-2-naphthol by iron(ni)284 and of 1-naphthol methyl ether by peroxyformic acid285 into the derived 1,1 -binaphthalene derivatives. 

Oxidation of 1-naphthol methyl ether A mixture of hydrogen peroxide solution (1.65 ml, containing 0.0165 mole of the peroxide) and formic acid (25 ml) is added during 90 min to a stirred solution of the ether (2.37 g, 0.015 mole) in 98-100% formic acid (75 ml) at 40°. After a few minutes the solution becomes red, and precipitation of crystals begins within 30 min. The mixture is stirred for 15 min after addition of the peroxide-formic acid solution and is then set aside at room temperature for 12 h. The crystals of 4,4/-dimethoxy-l,l/-bi-naphthalene are collected and washed with a little ethanol, then having m.p. 256-257° (l-35g). Concentrating the mother-liquor gives a small further batch (0.3 g). The total yield is 70%. 

Methyl 2-naphthyl sulphide 2-Thio-naphthol methyl ether)... 

Naphthyl methyl ether (nerolin). Use 36 0 g. of p-naphthol, 10-5 g. of sodium hydroxide in 150 ml. of water, and add 31 -5 g. (23 -5 ml.) of dimethyl sulphate whilst the mixture is cooled in ice. Warm for 1 hour at 70-80°, and allow to cool. Filter oflF the naphthyl methyl ether at the pump, wash with 10 per cent, sodium hydroxide solution, then liberally with water, and drain thoroughly. Recrystallise from benzene or methylated spirit. The yield is 33 g., m.p. 72°. 

Naphthalene, 216 Naphthalene picrate, 217 Naphthalene sulphonaie ofsodiiim, 218-/ J-Naphthol, 219 Naphthol yellow, 224 /i Naphthyl acetate, 222 /j-Naphthyl methyl ether, 220 /-Nitracetanilide, 153 w-Nitraniline, 154 /-Nitraniline, 153 Nitric acid (fuming), 22 NitroVienzene, 142 w-Nitrobenzoic acid, 200 Nitrogen, qualitative e rimation, 2 quantitative estimation, 13 Nitrophenol, 183 Nitrosohenzene, 146 /-Nitrosodimethylaniline, 157 Niirosoplienol, 159... 

In 1988 Masoud and Ishak demonstrated that ( -arenediazo methyl ethers do not react with 2-naphthol in dry organic solvents such as dioxan, ethanol, 2-propanol, but only in the presence of water. The reactions are catalyzed by hydrochloric acid (even in the absence of water). Under such conditions almost quantitative yields of azo compounds were obtained. A careful and extensive kinetic investigation of the HCl-catalyzed dediazoniation of substituted benzenediazo methyl ethers, varying the HC1 concentration and the diazo ether/2-naphthol ratio (the latter either absent or in large excess), and comparing the observed rate constants with Hammett s acidity functions for dioxane and ethanol (see Rochester, 1970) indicated the mechanism shown in Schemes 12-8 to 12-10 (DE = diazo methyl ether, D+ = diazonium ion). 

The first step was found to be a fast pre-equilibrium (Scheme 12-8). The dependence of the measured azo coupling rate constants on the acidity function and the effect of electron-withdrawing substituents in the benzenediazo methyl ether resulting in reduced rate constants are consistent with a mechanism in which the slow step is a first-order dissociation of the protonated diazo ether to give the diazonium ion (Scheme 12-9). The azo coupling proper (Scheme 12-10) is faster than the dissociation, since the overall rate constant is found to be independent of the naphthol con-... 

The crucial requirement of excited-state proton transfer (ESPT) is suggested by the failure of 1-naphthyl methyl ether to undergo self-nitrosation under similar photolysis conditions. The ESPT is further established by quenching of the photonitrosation as well as 1-naphthol fluorescence by general bases, such as water and triethylamine, with comparable quenching rate constants and quantum yield. ESPT shows the significance in relation to the requirement of acid in photolysis of nitrosamines and acid association is a photolabile species. 

Tetralone has been prepared by a variety of methods, but the only practical procedures are relatively recent ones involving reduction of /9-naphthyl methyl ether with sodium and alcohol2 or with sodium and liquid ammonia,3 high-pressure catalytic hydrogenation of /9-naphthol,4 or catalytic oxidation of 2-tetralol by hydrogen transfer with ethylene.6... 

This substance melts at 244° to 245° C. The corresponding products with f3-naphthol aldehyde and its methyl ether melt at 210° to 211° C. and 127° to 128° C. respectively. 

Other methyl ethers may be prepared in a similar manner e.g., f-naphthyl methyl ether (M.P. 71°) is formed in good yield from /3-naphthol. 

Raney nickel catalyst W-5, 32, 59 Reduction, and amidation of methyl 7-methyl-y-nitrovalerate, 32, 59 and hydrolysis of -naphthol ethyl ether, 32, 97... 

Chow et al. developed the photocycloaddition of acetylacetone (87) with naphthols (86a, 88a) and their methyl ethers (86b, 88b) [141] (Scheme 28). The cyclization occurs regiospecifically to give diketones with low quantum efficiency. Whereas the excitation of the naphthol component does not take place during photoreaction, the excitation of the acetylacetone component leads to the formation of photocycloadducts. 

According to that author, such a typical aromatic nitro compound as 4-nitro-1-naphthol (VII) when reacted with diazomethane, formed not only methyl ether (VIII) but also quinone oxime (IX) in lower yield (16%) ... 

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