ChemicalBook CAS DataBase List 1-Naphthol

1-Naphthol synthesis

7synthesis methods

Product Name:1-Naphthol
CAS Number:90-15-3
Molecular formula:C10H8O
Molecular Weight:144.17

2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%.

13922-41-3 Synthesis

13922-41-3
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$5.00/1g

90-15-3
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$9.00/5g

Yield:90-15-3 98%

Reaction Conditions:

with dihydrogen peroxide at 30; for 5 h;Green chemistry;

Steps:

General procedure for the oxidation of boronic acids

General procedure: A mixture of boronic acid (1mmol), DMC (1.0mL) was taken in 25mL round bottom flask with magnetic stirring bar. Then the reaction was activated by addition of 30% H₂O₂ (2.0equiv.) and stirred at room temperature for 5h. The progress of reaction was monitored by TLC. After disappearance of starting material, added H₂O (1.0mL) in to the reaction mixture. The reaction mixture was then further diluted with ethyl acetate (30mL) and subsequently washed with distilled water (5.0mL). The resulting organic extract was dried over anhydrous sodium sulphate. The solvent was removed under vacuum to get crude product which was purified (if necessary) by column chromatography using silica gel with pet ether and ethyl acetate as solvent system to obtain the pure product. The structure of the product was confirmed by GC-MS, M.P. and ¹H NMR spectroscopic techniques.

References:

Wagh, Ravindra B.;Nagarkar, Jayashree M. [Tetrahedron Letters,2017,vol. 58,# 48,p. 4572 - 4575] Location in patent:supporting information