7163-25-9

Basic information

• Product Name: 3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester
• Synonyms: 3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester;3-Hydroxy-2-naphthoic acid ethyl ester;Ethyl 3-hydroxynaphthalene-2-carboxylate;2-Naphthalenecarboxylic acid, 3-hydroxy-, ethyl ester;3-Hydroxy-naphthalene-2-carboxylic acid ethyl ester
• CAS NO: 7163-25-9
• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.24
• Mol File: 7163-25-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 79.0 to 83.0 °C
• Boiling Point: 291°C(lit.)
• Appearance: /
• Density: 1.1652 (rough estimate)
• Refractive Index: 1.5090 (estimate)
• Solubility: soluble in Toluene
• PKA: 9.53±0.40(Predicted)
• CAS DataBase Reference: 3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester(7163-25-9)
• EPA Substance Registry System: 3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester(7163-25-9)

Safety Data

• Hazardous Substances Data: 7163-25-9(Hazardous Substances Data)

Usage

Uses

3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

To a round bottom flask were added 5 g 3-hydroxy-2-naphthalic acidand 16 mL ethanol. The reaction mixture was refluxed for 6 h. After thecompletion of the reaction, the reaction mixture was cooled down to room temperature and washed with distilled water. The organic layerwas recovered and washed with saturated sodium bicarbonate followedby drying with anhydrous MgSO4. The MgSO4 was removed by filtrationand the filtrate was dried under reduced pressure. The resulted solid waspurified by silica chromatography with petroleum ether and ethyl acetate(10:1, v/v) as eluent to give the compound ethyl 3-hydroxy-2-naphthoate(4.1229 g, yield 70.60%).

Upstream product

• 64-17-5 ethanol 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 64-67-5 diethyl sulfate 
• 288402-18-6 methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate 
• 10576-12-2 ethyl acetohydroximate 
• 7664-93-9 sulfuric acid 
• 3007-91-8 ethyl-2-naphthoate 

Downstream Products

• 3665-51-8 3-hydroxy-2-naphthalenecarboxamide 
• 91901-71-2 3-hydroxy-4-nitro-[2]naphthoic acid ethyl ester 
• 5341-58-2 3-hydroxy-2-naphthohydrazide 
• 75001-03-5 1-(4-diethylaminophenylazo)-3-carbethoxy-2-hydroxynaphthalene 
• 887281-74-5 ethyl 3-(5-chloro-2-nitrophenyloxy)-2-naphthoate 
• 52449-77-1 3-hydroxy-2-naphthonitrile 
• 362608-10-4 3-hydroxy-N′-[1-(pyridin-3-yl)ethylidene]-2-naphthohydrazide 
• 363597-19-7 3-hydroxy-N′-[1-(pyridin-2-yl)ethylidene]-2-naphthohydrazide 
• 65550-19-8 3-prop-2-enoxynaphthalene-2-carboxylic acid 
• 1287287-04-0 C₅₀H₄₇NO₁₁S 
• 86602-78-0 12-phenyl-12H-benzo[b]xanthene 
• 68181-06-6 3-hydroxy-N'-benzylidene-2-naphthohydrazide 

Relevant articles and documents

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Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade

A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.