6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester
• CAS No.: 895520-97-5
• Molecular Formula: C₂₄H₂₆O₃
• Molecular Weight: 362.469
• Mol file: 895520-97-5.mol

Synonyms:6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester

Chemical Property of 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester

There total 6 articles about 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl 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: 87.0%

6-(1-ethylpropenyl)naphthalene-2-carboxylic acid methyl ester + ortho-cresol (95-48-7,77504-84-8) → 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (895520-97-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 16h;

Reference yield:

methyl 6-((phenylsulfonyl)methyl)-2-naphthoate → 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (895520-97-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium ethanolate; dicyclohexyll(2,2'',4,4'',6,6''-hexaisopropyl-[1,1':3',1''-terphenyl]-5'-yl)phosphine / toluene / 16 h / 85 °C / Sealed tube; Glovebox; Inert atmosphere

3.1: boron tribromide / dichloromethane / 17.5 h / -78 - 20 °C / Inert atmosphere

4.1: sulfuric acid / 16 h / 75 °C / Inert atmosphere

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sulfuric acid; dicyclohexyll(2,2'',4,4'',6,6''-hexaisopropyl-[1,1':3',1''-terphenyl]-5'-yl)phosphine; sodium ethanolate; sodium hexamethyldisilazane; boron tribromide; In tetrahydrofuran; dichloromethane; toluene; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jacs.7b10855

Reference yield:

methyl 6-(3-(phenylsulfonyl)pentan-3-yl)-2-naphthoate → 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (895520-97-5)

Guidance literature:

Multi-step reaction with 3 steps

1: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium ethanolate; dicyclohexyll(2,2'',4,4'',6,6''-hexaisopropyl-[1,1':3',1''-terphenyl]-5'-yl)phosphine / toluene / 16 h / 85 °C / Sealed tube; Glovebox; Inert atmosphere

2: boron tribromide / dichloromethane / 17.5 h / -78 - 20 °C / Inert atmosphere

3: sulfuric acid / 16 h / 75 °C / Inert atmosphere

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sulfuric acid; dicyclohexyll(2,2'',4,4'',6,6''-hexaisopropyl-[1,1':3',1''-terphenyl]-5'-yl)phosphine; sodium ethanolate; boron tribromide; In dichloromethane; toluene; 1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jacs.7b10855

upstream raw materials:

ortho-cresol

methanol

methyl 6-(bromomethyl)naphthalene-2-carboxylate