Benzaldehyde, 2-(3-phenyl-2-propynyl)-

Base Information

• Chemical Name: Benzaldehyde, 2-(3-phenyl-2-propynyl)-
• CAS No.: 267668-92-8
• Molecular Formula: C16H12O
• Molecular Weight: 220.271
• Mol file: 267668-92-8.mol

Synonyms:

Chemical Property of Benzaldehyde, 2-(3-phenyl-2-propynyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzaldehyde, 2-(3-phenyl-2-propynyl)-

There total 12 articles about Benzaldehyde, 2-(3-phenyl-2-propynyl)- 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: 85.0%

2-[2'-(3-phenylprop-2-ynyl)phenyl]-1,3-dioxolane (267668-87-1) → 2-(3-phenylprop-2-yn-1-yl)benzaldehyde (267668-92-8)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 2h; Reflux;

DOI:10.1039/c4ob01583e

Reference yield: 48.0%

o-bromobenzaldehyde dimethyl acetal (35849-09-3) + 1-bromo-3-phenylprop-2-yne (1794-48-5) → 2-(3-phenylprop-2-yn-1-yl)benzaldehyde (267668-92-8)

Guidance literature:

With magnesium; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1246/BCSJ.20190301

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → 2-(3-phenylprop-2-yn-1-yl)benzaldehyde (267668-92-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: PTSA

2.1: n-BuLi

2.2: MgBr₂

3.1: KF; NH₄Cl; NBu₄HSO₄

4.1: PdCl₂(PPh₃)2; CuI; NEt₃

5.1: aq. PTSA / acetone

With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; copper(l) iodide; n-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; toluene-4-sulfonic acid; triethylamine; In acetone; 1.1: Condensation / 2.1: Substitution / 2.2: Grignard reaction / 2.3: Substitution / 3.1: desilylation / 4.1: Arylation / 5.1: Hydrolysis;

DOI:10.1021/ol0056832

upstream raw materials:

2-[2'-(3-phenylprop-2-ynyl)phenyl]-1,3-dioxolane

iodobenzene

2-[2-(prop-2-ynyl)phenyl]-1,3-dioxolane

2-(2-bromophenyl)-1,3-dioxolan

Downstream raw materials:

C₁₇H₁₅NO

methyl{[2'-(3-phenylprop-2-ynyl)phenyl]methylene}amine N-oxide

tert-butyl{[2'-(3-phenylprop-2-ynyl)phenyl]methylene}amine N-oxide

N-{[2'-(3-phenylprop-2-ynyl)phenyl]methylene}aniline N-oxide

Refernces

• 1、 Hu, Yue,Huang, Hanmin. "Highly selective construction of medium-sized lactams by palladium-catalyzed intramolecular hydroaminocarbonylation of aminoalkynes". supporting information. p. 5070 - 5073. Retrieved 2017/11/07.
• 2、 Dell'Acqua, Monica,Pirovano, Valentina,Confalonieri, Giorgio,Arcadi, Antonio,Rossi, Elisabetta,Abbiati, Giorgio. "Synthesis of 3-benzylisoquinolines by domino imination/cycloisomerisation of 2-propargylbenzaldehydes". . p. 8019 - 8030. Retrieved 2015/01/08.