Naphthol Naphthyl 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... 

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... 

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. 

Other methyl ethers may be prepared by a similar procedure. /3-Naphthyl methyl ether is obtained in a 65-73 per cent yield by adding the dimethyl sulfate over a period of thirty minutes to equivalent quantities of /3-naphthol and sodium hydroxide kept cool by an ice-water bath, then heating for one hour at 75-78°, and, finally, crystallizing from benzene to obtain the pure methyl ether which melts at 71°. 

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,... 

Alcohols. Methanol and ethanol have long been important alkylating agents, especially for nitrogen bonding. In practically every case, a catalyst is necessary to cause the alkylation to proceed smoothlyvand in many instances, this is a mineral acid. Alcohols are used in the manufacture of ethers, such as ordinary ethyl ether, isopropyl ether, Carbitol, Cellosolve, and naphthyl methyl ether. It should be noted that, although naphthols react with alcohol in the presence of a mineral acid, the aryl alkyl ethers cannot be formed by this reaction in the case of phenols. 

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-[ 5,7-dinitro-8-hydroxy-naphthyl-(l)] -ether, 2,4-Dinitro-8-methoxy-naphthol-(l) ). (02N)2CioH4(OH).O.CH3, mw 264.21, N 10.61%, OB to C02 -121.12%, gold plates from ale, mp 179—80° (decompn). Sol in dil alkali ale. Prepn from 2,4-dinitro-1,8-dime thoxy-naphthalene by reaction with 2N NaOH Ref Beil 6, 5284 ... 

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

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

Conversion of phenols into their methyl or ethyl ethers by reaction with the corresponding alkyl sulphates in the presence of aqueous sodium hydroxide affords a method which avoids the use of the more expensive alkyl halides (e.g. the synthesis of methyl 2-naphthyl ether and veratraldehyde, Expt 6.111). Also included in Expt 6.111 is a general procedure for the alkylation of phenols under PTC conditions.38,39 The method is suitable for 2,6-dialkylphenols, naphthols and various functionally substituted phenols. The alkylating agents include dimethyl sulphate, diethyl sulphate, methyl iodide, allyl bromide, epichlorohy-drin, butyl bromide and benzyl chloride. 

Naphthyl methylethers are easily converted to methylnaphthols, 5). The a-isomer forms 2- and 4-methyl-a-naphthol, the j3-isomer only l-methyl- 3-naphthol. Ethers with alkyl groups other than methyl sometimes show side reactions due to fragmentation of the migrating group. For example, n-pro-pylphenylether yields mainly ortho- and para-n-propylphenol, but also some ethylphenols and cresols 14). 

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