8,9-Dehydrothymol

Base Information

• Chemical Name: 8,9-Dehydrothymol
• CAS No.: 18612-99-2
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• DSSTox Substance ID: DTXSID60423892
• Nikkaji Number: J799.019G
• Wikidata: Q82236218
• Mol file: 18612-99-2.mol

Synonyms:8,9-Dehydrothymol;2-isopropenyl-5-methylphenol;18612-99-2;5-methyl-2-prop-1-en-2-ylphenol;Phenol, 5-methyl-2-(1-methylethenyl)-;m-Cresol, 6-isopropenyl-;SCHEMBL686122;2-Isopropenyl-5-methyl-phenol;DTXSID60423892;IHWFPRKZRRGTTI-UHFFFAOYSA-N;5-Methyl-2-(1-methylethenyl)phenol;5-Methyl-2-(prop-1-en-2-yl)phenol

Chemical Property of 8,9-Dehydrothymol

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)C(=C)C)O

Technology Process of 8,9-Dehydrothymol

There total 33 articles about 8,9-Dehydrothymol 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: 94.0%

4'-hydroxy-2'-methylacetophenone (6921-64-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 2-isopropenyl-5-methylphenol (18612-99-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201701481

Reference yield: 90.0%

4,7-dimethyl-coumarin (14002-90-5) → 2-isopropenyl-5-methylphenol (18612-99-2) + thymol (89-83-8)

Guidance literature:

With potassium hydroxide; In ethylene glycol; for 1h; Mechanism; Reflux;

DOI:10.1016/j.tetlet.2012.09.122

Reference yield: 74.0%

4,7-dimethyl-coumarin (14002-90-5) → 2-isopropenyl-5-methylphenol (18612-99-2)

Guidance literature:

With sodium hydroxide; In ethylene glycol; for 2h; Heating;

DOI:10.1080/00304940009356753

upstream raw materials:

2,2-bis(2'-hydroxy-4'-methylphenyl)propane

isopropenyl-m-tolyl ether

2-Hydroxy-α,α,4-trimethylbenzyl alcohol

3-ethoxyprop-1-ene

Downstream raw materials:

thymol

2-(2'-Acetoxy-4'-methylphenyl)-prop-2-enal

4,7-dimethyl-coumarin

ethyl α-(2-hydroxyisopropenyl-5-methyl phenoxy) propionate

Refernces

• 1、 -. "Thymol, and preparation method and pharmaceutical composition thereof". Paragraph 0058; 0066; 0074; 0082; 0088; 0090. . Retrieved 2019/01/07.
• 2、 Ferguson, Jamie,Zeng, Fanlong,Alper, Howard. "Synthesis of coumarins via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylphenols". supporting information. p. 5602 - 5605,4. Retrieved 2012/12/12.