2-Methoxynaphthalene

Description

β-Naphthyl methyl ether has an intensely sweet, floral odor suggestive of orange blossoms. It is free from naphthol by-odor. It has a sweet, strawberry taste. This may be prepared from potassium β-naphthol and methyl chloride at 300°C; by methylation of β-naphthol with dimethyl sulfate or by direct esterification with methyl alcohol.

Chemical properties

white powder

Chemical properties

Methyl 2-Naphthyl Ether forms white crystals (mp 73–74°C) with an intense orange blossom odor.

Chemical properties

β-Naphthyl methyl ether has an intensely sweet, floral odor suggestive of orange blossoms; free from naphthol by-odor. It has a sweet, strawberry taste

The Uses of 2-Methoxynaphthalene

2-Methoxynaphthalene is an Impurity of the non-steroidal anti-inflammatory Naproxen (N377525).

The Uses of 2-Methoxynaphthalene

2-methoxynaphthalene acylation is used as a model reaction to study the catalytic benefits of delamination. It was also used to study the alkali-metal-mediated manganation (AMMMn) reactions.

The Uses of 2-Methoxynaphthalene

2-methoxynaphthalene acylation was used as a model reaction to study the catalytic benefits of delamination. It was also used to study the alkali-metal-mediated manganation (AMMMn) reactions.

Preparation

From postassium β-naphthol and methyl chloride at 300°C; by methylation of β-naphthlol with dimethyl sulfate or by direct esterification with methyl alcohol

Definition

ChEBI: 2-Methoxynaphthalene is a member of naphthalenes.

Synthesis Reference(s)

Tetrahedron, 48, p. 6439, 1992 DOI: 10.1016/S0040-4020(01)88233-8
Tetrahedron Letters, 22, p. 3463, 1981 DOI: 10.1016/S0040-4039(01)81932-8

Flammability and Explosibility

Not classified

Synthesis

Preparation of 2-Methoxynaphthalene from 2-naphthol.
Principle: Phenols can be methylated to give methyl ethers. Methylation can be done either by using diazomethane or dimethyl sulphate in alkaline medium.
Reaction:

Procedure: Take 0.5 g 2-naphthol and 0.2 g NaOH in 5 ml distilled water in a beaker (25 ml). Heat on a wire gauze to obtain a clear solution. Cool the solution (10-15°C) and then add 0.35 ml dimethyl sulphate drop wise. After the addition is over, warm the mixture for one hour at 70-80°C and then cool. Filter the product and wash it with 10% sodium hydroxide solution and then with water. Dry the product, record the practical yield and re-crystallize it.
Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. Filter the white crystals of the product. Dry and record the melting point and TLC (using toluene as solvent).

Purification Methods

Fractionally distil the ether under vacuum. Crystallise it from absolute EtOH, aqueous EtOH, *C6H6, pet ether or n-heptane, and dry it under vacuum in an Abderhalden pistol or distil it in vacuo. The picrate has m 118o (from EtOH or CHCl3). [Kikuchi et al. J Phys Chem 91 574 1987, Beilstein 6 III 2969, 6 IV 4257.]