(2-Allyl-3-methoxyphenyl)methanol

Base Information

• Chemical Name: (2-Allyl-3-methoxyphenyl)methanol
• CAS No.: 136911-16-5
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID40459018
• Wikidata: Q82282611
• Mol file: 136911-16-5.mol

Synonyms:(2-Allyl-3-methoxyphenyl)methanol;136911-16-5;(3-methoxy-2-prop-2-enylphenyl)methanol;2-allyl-3-methoxybenzyl alcohol;SCHEMBL4981005;DTXSID40459018;ISHSNXMXBLGLCF-UHFFFAOYSA-N;SB85252;A921051

Chemical Property of (2-Allyl-3-methoxyphenyl)methanol

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 156

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC(=C1CC=C)CO

Technology Process of (2-Allyl-3-methoxyphenyl)methanol

There total 6 articles about (2-Allyl-3-methoxyphenyl)methanol 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: 88.0%

2-allyl-3-methoxybenzyl 3,5-dinitrobenzoate (1613271-10-5) → (2-allyl-3-methoxyphenyl)methanol (136911-16-5)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 - 37.7 ℃; for 1h; Large scale;

Reference yield:

2-allyl-3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol (223734-55-2) → (2-allyl-3-methoxyphenyl)methanol (136911-16-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(01)80765-1

Reference yield:

3-methoxybenzyl alcohol (6971-51-3) → (2-allyl-3-methoxyphenyl)methanol (136911-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / imidazole / CH₂Cl₂

2: n-BuLi / hexane / 24 h / 0 - 20 °C

3: 4695 g / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo0347720

upstream raw materials:

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

allyl bromide

2-allyl-3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

3-methoxybenzyl alcohol

Downstream raw materials:

o-(chloromethyl)-2-allylanisole

2-allyl-3-methoxybenzaldehyde

treprostinil

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol

Refernces

• 1、 -. "METHODS OF SYNTHESIZING A PROSTACYCLIN ANALOG". Paragraph 0354-0355. . Retrieved 2014/06/24.
• 2、 Moriarty, Robert M.,Rani, Neena,Enache, Livia A.,Rao, Munagala S.,Batra, Hitesh,Guo, Liang,Penmasta, Raju A.,Staszewski, James P.,Tuladhar, Sudersan M.,Prakash, Om,Crich, David,Hirtopeanu, Anca,Gilardi, Richard. "The Intramolecular Asymmetric Pauson-Khand Cyclization As A Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil)". . p. 1890 - 1902. Retrieved 2007/10/03.