Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate

Base Information

• Chemical Name: Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate
• CAS No.: 81113-20-4
• Molecular Formula: C₁₉H₁₆O₃
• Molecular Weight: 292.334
• DSSTox Substance ID: DTXSID301235314
• Nikkaji Number: J337.834I
• Mol file: 81113-20-4.mol

Synonyms:DTXSID301235314;AS-0457;Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate;ethyl 1-hydroxy-4-phenylnaphthalene-2-carboxylate;81113-20-4

Chemical Property of Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 292.109944368
• Heavy Atom Count: 22
• Complexity: 375

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=CC=CC=C2C(=C1)C3=CC=CC=C3)O

Technology Process of Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate

There total 10 articles about Ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ethyl 2-bromo-3-oxo-3-phenylpropionate (55919-47-6) + phenylacetylene (536-74-3) → ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate (81113-20-4)

Guidance literature:

With disodium hydrogenphosphate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Solvent; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Irradiation;

DOI:10.1021/ol402325z

Reference yield: 87.0%

diethyl 3,3-diphenylprop-2-ene-1,1-dicarboxylate (81113-21-5) → ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate (81113-20-4)

Guidance literature:

With molecular sieve; In toluene; at 140 ℃; for 60h;

DOI:10.1039/P19810003132

Reference yield: 85.0%

ethyl 3-oxo-3-phenylpropionate (94-02-0) + phenylacetylene (536-74-3) → ethyl 1-hydroxy-4-phenyl-2-naphthalenecarboxylate (81113-20-4)

Guidance literature:

With tert.-butylhydroperoxide; N-bromophthalimide; 2-bromoethylamine hydrobromide; In 1,4-dioxane; ethanol; water; at 90 ℃; for 20h; Reagent/catalyst; regioselective reaction; Catalytic behavior;

DOI:10.1021/acs.orglett.7b03186

upstream raw materials:

diethyl 3,3-diphenylprop-2-ene-1,1-dicarboxylate

C₁₇H₁₅IO₃

phenylacetylene

Diphenylacetaldehyde

Downstream raw materials:

1-hydroxy-4-phenyl-2-naphthoic acid