2-methoxy-5-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

Base Information

• Chemical Name: 2-methoxy-5-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione
• CAS No.: 80464-91-1
• Molecular Formula: C12H14 O3
• Molecular Weight: 206.241
• Mol file: 80464-91-1.mol

Synonyms:2,5-Cyclohexadiene-1,4-dione,2-methoxy-5-(3-methyl-2-butenyl)- (9CI); 5-Prenyl-2-methoxy-1,4-benzoquinone;NSC 339888

Chemical Property of 2-methoxy-5-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

Chemical Property:

• Vapor Pressure: 0.000396mmHg at 25°C
• Boiling Point: 317°C at 760 mmHg
• Flash Point: 138.2°C
• Density: 1.09g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-methoxy-5-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione

There total 11 articles about 2-methoxy-5-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione 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: 80.0%

2-methoxy-5-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol (127757-24-8) → 2-methoxy-5-(3'-methyl-2'-butenyl)-1,4-benzoquinone (80464-91-1)

Guidance literature:

With disodium hydrogenphosphate; sodium dihydrogenphosphate; potassiuim nitrosodisulfonate; triisooctyl amine; In dichloromethane; water; Ambient temperature;

DOI:10.1021/jo00054a012

Reference yield:

5-(3'-hydroxy-3'-methylbutenyl)-2-methoxy-4-<(dimethylamino)methyl>phenol (127757-17-9) → 2-methoxy-5-(3'-methyl-2'-butenyl)-1,4-benzoquinone (80464-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / tetrahydrofuran / 2 h / Ambient temperature

2: Li, NH₃ / tetrahydrofuran / 0.25 h / -78 °C

3: 80 percent / Fremy's salt, Na₂HPO₄, NaH₂PO₄ / Adogen / CH₂Cl₂; H₂O / Ambient temperature

With disodium hydrogenphosphate; sodium dihydrogenphosphate; potassiuim nitrosodisulfonate; ammonia; lithium; triethylamine; triisooctyl amine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00054a012

Reference yield:

4-((dimethylamino)methyl)-2-methoxyphenol (19861-69-9) → 2-methoxy-5-(3'-methyl-2'-butenyl)-1,4-benzoquinone (80464-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) LiPdCl₄, NaOAc, 2) NEt₃ / 1a) MeOH, 0 deg C, 10 min, 1b) r.t., 24 h, 2a) glac. acetic acid, CHCl₃, 0 deg C, 10 min, 2b) r.t., 24-48 h

2: hexane; benzene / 2 h / Ambient temperature

3: NEt₃ / tetrahydrofuran / 2 h / Ambient temperature

4: Li, NH₃ / tetrahydrofuran / 0.25 h / -78 °C

5: 80 percent / Fremy's salt, Na₂HPO₄, NaH₂PO₄ / Adogen / CH₂Cl₂; H₂O / Ambient temperature

With disodium hydrogenphosphate; sodium dihydrogenphosphate; lithium pentachloropalladate; potassiuim nitrosodisulfonate; ammonia; sodium acetate; lithium; triethylamine; triisooctyl amine; In tetrahydrofuran; hexane; dichloromethane; water; benzene;

DOI:10.1021/jo00054a012

upstream raw materials:

2-methoxy-5-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol

2-methoxy-5-(3-methyl-2-butenyl)hydroquinone

2-methyl-3-buten-2-ol

methoxyhydroquinone

Downstream raw materials:

precocene II

6-hydroxy-7-methoxy-2,2-dimethylchromen

Refernces

• 1、 Uchiyama, M.,Overeem, J. C.. "Prenylation of methoxyhydroquinone in aqueous acid solution and an alternative synthesis of precocene II". . p. 408 - 410. Retrieved 2007/10/02.