1H-Phenalen-1-one, 2-hydroxy-9-(4-methoxyphenyl)-

Base Information

• Chemical Name: 1H-Phenalen-1-one, 2-hydroxy-9-(4-methoxyphenyl)-
• CAS No.: 65874-44-4
• Molecular Formula: C20H14O3
• Molecular Weight: 302.329
• Mol file: 65874-44-4.mol

Synonyms:

Chemical Property of 1H-Phenalen-1-one, 2-hydroxy-9-(4-methoxyphenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Phenalen-1-one, 2-hydroxy-9-(4-methoxyphenyl)-

There total 9 articles about 1H-Phenalen-1-one, 2-hydroxy-9-(4-methoxyphenyl)- 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: 83.0%

2,3-epoxi-9-(4-methoxyphenyl)phenalen-1-one → 2-hydroxy-9-(4'-methoxyphenyl)-1H-phenalen-1-one (65874-44-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0040-4020(95)00129-V

Reference yield:

(1R*,2S*,3R*)-2,3-dihydro-1,2,3-trihydroxy-4-(4'-methoxyphenyl)-1H-phenalene → 2-hydroxy-9-(4'-methoxyphenyl)-1H-phenalen-1-one (65874-44-4) + 2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (159853-36-8)

Guidance literature:

With jones reagent; sulfuric acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) acetone, water, 15 min, 2.) acetone, water, 15 min;

DOI:10.1016/0040-4020(95)00129-V

Reference yield:

1-naphthaldehyde (66-77-3) → 2-hydroxy-9-(4'-methoxyphenyl)-1H-phenalen-1-one (65874-44-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 - 25 °C / Inert atmosphere

1.2: 12 h / 20 - 25 °C / Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 12 h / 40 °C / Inert atmosphere

2.2: 20 - 25 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane / 0.17 h / Inert atmosphere

3.2: 20 - 25 °C / Inert atmosphere

4.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C / Inert atmosphere

5.1: tetrahydrofuran / -10 - 25 °C / Inert atmosphere

5.2: 3 h / Inert atmosphere; Reflux

6.1: N-benzyl-trimethylammonium hydroxide; tert.-butylhydroperoxide / methanol; water; toluene / 4 h / -5 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / toluene / Inert atmosphere

With tert.-butylhydroperoxide; aluminum (III) chloride; oxalyl dichloride; potassium tert-butylate; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 4.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.jnatprod.7b00709

upstream raw materials:

1-naphthaldehyde

(E)-3-(naphthalen-1-yl)acrylic acid

(E)‐3‐(naphthalen‐1‐yl)acryloyl chloride

Perinaphthenon

Downstream raw materials:

2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one