2,2'-Dimethoxy-6-formylbiphenyl

Base Information

• Chemical Name: 2,2'-Dimethoxy-6-formylbiphenyl
• CAS No.: 87306-84-1
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.274
• DSSTox Substance ID: DTXSID00525642
• Wikidata: Q82393387
• Mol file: 87306-84-1.mol

Synonyms:2,2'-DIMETHOXY-6-FORMYLBIPHENYL;87306-84-1;DTXSID00525642;2',6-Dimethoxy[1,1'-biphenyl]-2-carbaldehyde;2',6-DIMETHOXY-[1,1'-BIPHENYL]-2-CARBALDEHYDE

Chemical Property of 2,2'-Dimethoxy-6-formylbiphenyl

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 267

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC=C1C2=C(C=CC=C2OC)C=O

Technology Process of 2,2'-Dimethoxy-6-formylbiphenyl

There total 18 articles about 2,2'-Dimethoxy-6-formylbiphenyl 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: 63.0%

[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethyl-2-phenyl-ethyl]-[1-(6,2'-dimethoxy-biphenyl-2-yl)-meth-(E)-ylidene]-amine (87306-98-7,94293-37-5,94293-38-6) → 2',6-dimethoxy-(1,1'-biphenyl)-2-carboxaldehyde (87306-84-1,94235-94-6,94235-95-7)

Guidance literature:

With oxalic acid; In pentane; for 12h; Ambient temperature;

DOI:10.1021/ja00289a023

Reference yield:

2,3-dimethoxybenzoic acid (1521-38-6) → 2',6-dimethoxy-(1,1'-biphenyl)-2-carboxaldehyde (87306-84-1,94235-94-6,94235-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl chloride / CH₂Cl₂ / 14 h

2: 30 percent NH₄OH

3: 1.) triethyloxonium tetrafluoroborate / 1.) 1,2-dichloroethane, 22 h; 2.) 1,2-dichloroethane, 24 h, reflux

4: 1.) Mg / 1.) ether, 1 h; 2.) ether, THF, 24 h

5: 1 M DIBAL / diethyl ether / Ambient temperature

6: tetrahydrofuran / 12 h / Ambient temperature

7: N-chlorosuccinimide / CH₂Cl₂ / 0.25 h

8: potassium superoxide / 18-crown-6 / diethyl ether / Ambient temperature

9: 63 percent / oxalic acid / pentane / 12 h / Ambient temperature

With potassium superoxide; ammonium hydroxide; N-chloro-succinimide; oxalyl dichloride; triethyloxonium fluoroborate; oxalic acid; diisobutylaluminium hydride; magnesium; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja00289a023

Reference yield:

(4S,5S)-2-(6,2'-Dimethoxy-biphenyl-2-yl)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazole (87306-76-1) → 2',6-dimethoxy-(1,1'-biphenyl)-2-carboxaldehyde (87306-84-1,94235-94-6,94235-95-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1 M DIBAL / diethyl ether / Ambient temperature

2: tetrahydrofuran / 12 h / Ambient temperature

3: N-chlorosuccinimide / CH₂Cl₂ / 0.25 h

4: potassium superoxide / 18-crown-6 / diethyl ether / Ambient temperature

5: 63 percent / oxalic acid / pentane / 12 h / Ambient temperature

With potassium superoxide; N-chloro-succinimide; oxalic acid; diisobutylaluminium hydride; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja00289a023

upstream raw materials:

[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethyl-2-phenyl-ethyl]-[1-(6,2'-dimethoxy-biphenyl-2-yl)-meth-(E)-ylidene]-amine

[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethyl-2-phenyl-ethyl]-[1-(6,2'-dimethoxy-biphenyl-2-yl)-meth-(E)-ylidene]-amine

2-methoxyphenyllithium

2,3-dimethyoxybenzaldehyde

Refernces

• 1、 Meyers, Albert I.,Flanagan, Mark E.. "2,2′-Dimethoxy-6-formylbiphenyl". . p. 107 - 107. Retrieved 2017/06/01.
• 2、 Meyers, A. I.,Himmelsbach, Richard J.,Reuman, Michael. "Reductive Cleavage of Aryl Oxazolines to Benzaldehydes and Substituted Toluenes". . p. 4053 - 4058. Retrieved 2007/10/02.