Methyl-2-naphthyl ether

Methyl 1-naphthyl ether [2216-69-5] M 158.2, b 90-91°/2mm, d 1.095, n26 1.6210. Steam distd from alkali. The distillate was extracted with ethyl ether. After drying the extract and evaporating the ethyl ether, the methyl naphthyl ether was distd under reduced pressure. 

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... 

Among more common aromatic ethers, monobromoderivatives are formed from o-cresyl methyl ether, ethyl 1-naphthyl ether, ethyl 2-naphthyl ether, and methyl 2-naphthyl ether dibromoderivatives from veratrol, resorcinol dimethyl ether, diphenyl ether, isoeugenol methyl ether, methyl 1-naphthyl ether, dibenzyl ether, ethyl 2-naphthyl ether, and hydroqui-none dimethyl ether and tribromoderivatives from anethol, eugenol methyl ether, isosafrol. 

Methoxy-Naphthalene (Methyl- -naphthyl-ether). Cryst, mp 73—74°, bp 274°. Sol in eth, chlf benz. Prepn from K- -napthalate by heating with methyl chloride at 300°... 

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. 

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

Methyl 2-Naphthyl Ether. (Nerolin.) C10H7OCH3. (Method 3, p. 218.)... 

Recrystallise from methylated spirit, from which the methyl 2-naphthyl ether separates readily as colourless crystals, m.p. 72° yield, 9 g. 

Naphthyl methyl ether.—Dissolve 3-6grams(3-naphthnl in I3 5 c.c. 10 per cent, caustic soda solution, add 3 c.c. meth l sulphate, warm the liquid gently and shake vigorously. In. i short time the naphthyl methyl ether separates as a solid mass. The product is heated for ten minutes on the water-bath, a little water is added, and the naphthyl ether filtered and washed with water. It is crystallised from alcohol and deposits in lustrous plates m. p. 70—72°. The yield is theoretical. It may be used for analysis by Zeisel s method. 

Dinitro-5-methoxy-naphthol-(l), methyl-[6,8-Dinitro-5-hydroxy-naphthyl-(])] -ether). (O2N)2C10H4(0H).O.CH3, mw 264.21, N 10.61%, OB to C02 —121.12%, orange needles from CCI4, mp 173° (decompn). Sol in CCI4. Prepn from 2,4-dinitro-naphthalenediol-(l,5) by reacting with an excess of dimethyl sulfate in dil NaOH... 

The difference in the electron affinity between light and heavy isotopic isomers is, in other words, the difference in the stability of their anion-radicals. Such a difference gives a valuable tool for use in probing the chemistry of anion-radicals. The difference in the stability of the ring-deuterated and ring-nondeuterated arene anion-radicals has been employed to examine the transition states for the one-electron-promoted cleavage of naphthyl methyl phenyl ether and naphthyl benzyl ether (Guthrie and Shi 1990). In this reaction, the potassium salt of fluoranthene anion-radical was an electron donor ... 

Phenyl n-propyl et.her. Phenyl n-butyl ether o-Cresyl methyl ether (1) m-Cresyl methyl ether. p-Cresyl methyl ether. o-Cresyl ethyl ether m-Cresyl ethyl ether p-Cresyl ethyl ether Benzyl methyl ether Benzyl ethyl ether Methyl a-naphthyl ether Methyl p-naphthyl ether Ethyl a-naphthyl ether Ethyl p-naphthyl ether Benzyl a-naphthyl ether Benzyl P-naphthyl ether o-Methoxydiphenyl p-Methoxydiphenyl. o-Chloroanisole. m-Chloroanisole. p-Chloroanisolc o-Bromoanisole m-Bromoanisole. p-Bromoanisole. o-Iodoanisole m-Iodoanisole p-Iodoanisole o-Nitroanisole... 

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. 

Experiment 6.111 METHYL 2-NAPHTHYL ETHER (Nerolin) 2-C10H7OH + NaOH + Me2S04------------ 2C10H7OMe + Na(Me)S04... 

Equip a 500-ml three-necked flask with a separatory funnel, a sealed mechanical stirrer and a reflux condenser. Place 36 g (0.25 mol) of 2-naphthol in the flask, add a solution of 10.5 g of sodium hydroxide in 150 ml of water and stir the mixture cool the warm mixture to about 10 °C by immersing the flask in an ice bath. Place 31.5 g (23.5 ml, 0.25 mol) of dimethyl sulphate (CAUTION see Section 4.2.24, p. 430) in the separatory funnel and add dropwise, during 1 hour, while stirring the mixture vigorously. Warm for 1 hour at 70-80 °C with stirring in order to complete the methylation. Allow to cool and filter off the methyl 2-naphthyl ether at the pump, wash with 10 per cent sodium hydroxide solution, then liberally with water and drain thoroughly. Recrystallise from industrial spirit. The yield is 33 g (84%), m.p. 72 °C. 

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