Nerolin

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

Nerolin, which has a faint but persistent odour, is used technically for scenting soaps, etc,... 

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°. 

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 = ... 

This substance is an artificial perfume having a neroli-like odour, and was introduced into commerce under the name yara-yara, and is also known as nerolin. It is a crystalline compound melting at 72° and boiling at 274°. Its constitution is—... 

Naphthyl Methyl Ether (Nerolin).—The procedure is the same as in the case of anisole, but the stoicheiometrical ratio is altered. Melting point 72°. The substance is crystalline. For a method by which it may be completely purified see Witt, Ber., 1901, 34, 3172. 

Strawberry Anisyl formate benzyl isobuiyrate Cuminic alcohol Ethyl methylphenylglycidaie Ethyl phenylglycidate Isoamyl salicylate Isobuiyl anthranilate Meihylacetophenone Methyl cinnamate. Methyl naphthyl ketone Nerolin Neryl isobutyrate Phenylglycidate... 

In this reaction, nitrobenzene as solvent has an important function because it causes acylation to occur predominantly at the 6-position, whereas l-acetyl-2-methoxynaphthalene is the principal product when carbon disulfide is used. The main feature of this procedure is the particular attention given to temperature control in order to obtain reliable results. It has been observed that the ratio of 6-acetylated to 1-acetylated nerolin is dependent on the temperature, the lower temperatures favoring 1 -acetylation. Below 0° the yield of 6-acetylated product is only 3-10%. At higher temperatures the 6-acetylated product predominates, but an increased amount of tarry material is formed. 

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

Orange flower chemicals Methyl napthyl ketone Nerolin bromelia... 

Honey notes Phenylethyl phenyl acetate Nerolin yara yara Linalyl phenylacetate... 

Dimethyl hydroquinone Nerolin yara yara Bromstyrol... 

Methylacetophenone Methyl anthralinate Methyl benzoate Methyl cinnamate Methyl hetine carbonate Methyl naphthyl ketone Methyl salicylate Mint essential oil Nerolin... 

The simple ether derivatives, 2-methoxy-naphthalene [CAS no. 93-04-9], nerolin, and 2-ethoxy-naphthalene [CAS no. 93-18-5] now are made easily by methylation (using dimethyl sulfate) or ethylation (using di-ethylsulfate) for use in perfume formulation and more recently as drugs intermediates. 

Methyl 2-naphthyl ether (2-methoxynaphthalene, Nerolin) [93-04-9] M 158.2, m 73.0-73.6°, b 138°/10mm 273°/760mm. Fractionally distil the ether under vacuum. Crystallise it from absolute EtOH, aqueous EtOH, C6H6, pet ether or -heptane, and dry it under vacuum in an Abderhalden pistol or distil it in vacuo. The picrate has m 118° (from EtOH or CHCI3). [Kikuchi et al. J Phys Chem 91 574 1987, Beilstein 6 III 2969, 6 IV 4257.]... 

Acetylation of naphthalene gives methyl naphthyl ketone, and sulfonation followed by alkaline fusion gives naphthol (Scheme 4.60). The methyl and ethyl ethers of naphthol are prepared from naphthol by reaction with the corresponding alkyl sulfate under basic conditions. These ethers are usually known by the shorter names of yara and nerolin, respectively. Yara, nerolin and methyl naphthyl ketone possess floral odours and are moderately important perfume ingredients. 

Ethoxynaphthalene. Ethyl (5 naphthyl ether ethyl d-naphtholate nerolin "new -naphthyl ethyl ether Bromelia, Cl2H]20 mol wt 172.22. C 83.09%, H 7.02%, O 9.29%. Prepd by heating d-naphthol with potassium ethyl sulfate, or with alcohol and HjS04 Yokoyama et of.. Yaku-%aku Zasshi 78, 123 (1958) C.A. 52, ]0986c (1958) from d-naphthol + p-toluenesulfonyl chloride + ethyl alcohol Drakowzal, Klamann, Monatsh 82, 5S8 (1951) from d-naphthol + H2S04 + ethyl acetate Patai, Bentov, J. Am. Cfiem. Soc. 74, 6118 (1952) From 6 -naphtha] + triethyl -phosphate + p-toluenesulfonic acid Bell, US. pat. 2,683,-748 (1954 ro Eastman Kodak). 

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,... 

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