Benzeneacetaldehyde, a-(1-methylethylidene)-

Base Information

• Chemical Name: Benzeneacetaldehyde, a-(1-methylethylidene)-
• CAS No.: 55106-21-3
• Molecular Formula: C11H12O
• Molecular Weight: 160.216
• Mol file: 55106-21-3.mol

Synonyms:

Chemical Property of Benzeneacetaldehyde, a-(1-methylethylidene)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzeneacetaldehyde, a-(1-methylethylidene)-

There total 13 articles about Benzeneacetaldehyde, a-(1-methylethylidene)- 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: 54.0%

4-phenyl-4-(prop-1-en-2-yl)-1,3-dioxolan-2-one → 3-Methyl-2-phenyl-2-butenal (55106-21-3)

Guidance literature:

With [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; bis[2-(diphenylphosphino)phenyl] ether; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.7b12608

Reference yield:

3-methyl-2-phenylbutyric acid (3508-94-9) → 3-Methyl-2-phenyl-2-butenal (55106-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂

2: H₂ / Pd-BaSO₄ / xylene

3: SO₂Cl₂ / CH₂Cl₂

4: LiClO₄, CaCO₃ / hexamethylphosphoric acid triamide / 120 - 130 °C

With thionyl chloride; sulfuryl dichloride; hydrogen; lithium perchlorate; calcium carbonate; palladium on barium sulfate; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; xylene;

Reference yield:

bromobenzene (108-86-1,52753-63-6) + 3,3-dimethyl acrylaldehyde (107-86-8) → 3-Methyl-2-phenyl-2-butenal (55106-21-3)

Guidance literature:

With sodium acetate; {Pd[P(o-C₆H₄CH₃)2(C₆H₄CH₂)][OCOCH₃]}2; In N,N-dimethyl acetamide; at 140 ℃; for 20h;

DOI:10.1002/adsc.200202180

upstream raw materials:

3-Methyl-2-phenyl-but-2-en-1-ol

Brom-1-methyl-3-phenyl-3-epoxy-1,2-butan

2-chloro-3-methyl-2-phenylbutanal

1-Phenyl-3-methyl-but-3-en-1,2-diol

Downstream raw materials:

2-Methyl-3-phenyl-2-hepten-5-yn-4-one

2-Methyl-3-phenyl-hept-2-en-5-yn-4-ol

Refernces

• 1、 Guo, Wusheng,Kuniyil, Rositha,Gómez, José Enrique,Maseras, Feliu,Kleij, Arjan W.. "A Domino Process toward Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative C(sp3)-C(sp3) Bond Formation". supporting information. p. 3981 - 3987. Retrieved 2018/03/29.
• 2、 Jacobi,Brielmann,Cann. "Enynones in organic synthesis. 7. Substituent effects on the α-tocopherol-catalyzed cyclization of enynones to methylenecyclopentenones. Convenient syntheses of members of the methylenomycin class of antibiotics". . p. 5305 - 5316. Retrieved 2007/10/02.