1-Methoxynaphthalene

Chemical properties

1-Methoxynaphthalene is an isomer of methoxynaphthalene. It is clear light yellow to brown liquid that aroma is not as good as 2-methoxynaphthalene. Insoluble in water, soluble in ethanol, ether, benzene and chloroform.

The Uses of 1-Methoxynaphthalene

1-Methoxynaphthalene is used in the study of peroxygenase activity of cytochrome c peroxidase. It is used as a precursor to synthesize prenyl naphthalene-ols, which shows antioxidative activity. It is also used in organic synthesis, pesticides, perfumes for making soaps, and film developers.

Preparation

1-Methoxynaphthalene can be obtained by methylating 1-naphthol, and the methylating reagent can be selected from methyl trifluoroacetate, dimethyl carbonate and dimethyl sulfate.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 675, 1991 DOI: 10.1016/S0040-4039(00)74857-X

General Description

1-Methoxynaphthalene, a methoxyphenolic compound, is a naphthalene derivative that finds application as a precursor for the preparation of pharmaceutical drugs, and also as a therapeutic agent.

Purification Methods

Steam distil the ether from alkaline solution. The distillate is extracted with Et2O. After drying (MgSO4) the extract and evaporating Et2O, the methyl naphthyl ether is then fractionated under reduced pressure from CaH2. The picrate has m 129.5-130.5o (from EtOH). [Beilstein 6 IV 4211.]