6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester

Base Information

• Chemical Name: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester
• CAS No.: 1334137-82-4
• Molecular Formula: C₂₀H₁₈O₃
• Molecular Weight: 306.361
• Mol file: 1334137-82-4.mol

Synonyms:ethyl 6-(4-methoxyphenyl)-2-naphthoate

Chemical Property of 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester

Chemical Property:

• Melting Point: 130-132 °C
• Boiling Point: 458.8±33.0 °C(Predicted)
• Density: 1.146±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

6-(4-Methoxyphenyl)-2-naphthoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 6-(4-Methoxyphenyl)-2-naphthoic Acid Ethyl Ester is an intermediate in the synthesis of Adapalene (A225000) metabolites.

Technology Process of 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester

There total 4 articles about 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid ethyl ester 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: 95.0%

6-(4-methoxyphenyl)-2-naphthoic acid (132292-17-2) + ethanol (64-17-5) → ethyl 6-(4-methoxyphenyl)-2-naphthoate (1334137-82-4)

Guidance literature:

With sulfuric acid; In toluene; at 78 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bioorg.2011.07.003

Reference yield:

4-methoxyphenylboronic acid (5720-07-0) + ethyl 6-bromo-naphthalene-2-carboxylate (86471-14-9) → ethyl 6-(4-methoxyphenyl)-2-naphthoate (1334137-82-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In ethanol; water; toluene; at 20 - 90 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201100207

Reference yield:

methyl 6-bromo-2-naphthoate (33626-98-1) → ethyl 6-(4-methoxyphenyl)-2-naphthoate (1334137-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / methanol / 8 h / 50 °C

2: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere

3: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere

With sulfuric acid; palladium 10% on activated carbon; sodium carbonate; potassium hydroxide; In methanol; water; toluene; 2: Suzuki coupling;

DOI:10.1016/j.bioorg.2011.07.003

upstream raw materials:

6-(4-methoxyphenyl)-2-naphthoic acid

ethanol

6-bromo-2-naphthoic acid

methyl 6-bromo-2-naphthoate

Downstream raw materials:

adapalene

C₃₃H₃₃BrN₂O₅

C₃₀H₂₈N₂O₅

C₁₈H₁₃ClO₂