Naphthols 6-methyl-2-naphthol

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... 

Let us now turn to compounds with more than one benzenoid ring. The first species are the isomeric a- and /J-naphthylamincs, 18a and 18b. The archival enthalpies of formation are found to be 157.6 6.9 and 133.8 5.1 kJmol-1. The 24 9 kJmol-1 difference of these two numbers is incompatible with the near-zero difference of the enthalpies of formation for the isomeric naphthols, methyl- and bromonaphthalenes32. Which or either naphthylamine has the correct enthalpy of formation The gas-phase enthalpies of formation of the naphthols differ from their single benzene ring analog, phenol, by 66 kJmol-1 in close agreement with the difference between the methylnaphthalenes and toluene, 63, and between the brominated and parent hydrocarbons, 69 6 and 68 2 kJmol-1 respectively. That is, it is plausibly asserted33 that the difference quantities 17 are nearly constant and equal. 

Photolytic. Based on data for phenol, a structurally related compound, an aqueous solution containing 1-naphthoxide ion (3 x 10 M) in room light would be expected to photooxidize to give 2-hydroxy-1,4-naphthoquinone (Tomkiewicz et al., 1971). 1-Naphthol, methyl isocyanate, and other unidentified cholinesterase inhibitors were reported as products formed from the direct photolysis of carbaryl by sunlight (Wolfe et al., 1976). In an aqueous solution at 25 °C, the photolysis half-life of carbaryl by natural sunlight or UV light (X = 313 nm) is 6.6 d (Wolfe et al, 1978a). 

Problem 19.30 (a) Give products, where formed, for reaction of PhN Cr with (i) a-naphthol, (ii) -naphthol, (iii) 4-methyl-l-naphthol, (iv) l-methyl-2-naphthol. (h) How can these products be used to make the corresponding aminonaphthols ... 

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. ... 

Phenol-methyl acetate Phenol-ethyl acetate Phenol-methylchloro acetate p-Chlorophenol-methyl acetate m-Chlorophenol-methyl acetate o-Chlorophenol-methyl acetate a-Naphthol-methyl acetate... 

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%. 

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... 

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

H BrjNO Dibnmunethyl-naphthocliiiiibol aus 4.6-I>ibrom-l-methyl-naphthol-(2)... 

A contact insecticide with the trade name Sevin . White solid, m.p. 142 C. It is prepared by reaction of I-naphthol with methyl isocyanate or with phosgene and a base. 

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