Dimesitylketene

Base Information

• Chemical Name: Dimesitylketene
• CAS No.: 87871-33-8
• Molecular Formula: C20H22O
• Molecular Weight: 278.394
• DSSTox Substance ID: DTXSID70552708
• Nikkaji Number: J401.832J
• Wikidata: Q82433076
• Mol file: 87871-33-8.mol

Synonyms:Dimesitylketene;87871-33-8;DTXSID70552708;Bis(2,4,6-trimethylphenyl)ethen-1-one;Bis-(2,4,6-trimethyl-phenyl)-ethenone

Chemical Property of Dimesitylketene

Chemical Property:

• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 278.167065321
• Heavy Atom Count: 21
• Complexity: 350

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)C2=C(C=C(C=C2C)C)C)C

Technology Process of Dimesitylketene

There total 9 articles about Dimesitylketene 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: 69.2%

2,2-bis(2,4,6-trimethylphenyl)acetic acid (5740-42-1) → bis(mesityl)ketene (87871-33-8)

Guidance literature:

With pyridine; thionyl chloride; In toluene; for 1h; Heating;

DOI:10.1039/P29920000927

Reference yield: 63.0%

dimesitylacetyl chloride (94203-61-9) → bis(mesityl)ketene (87871-33-8)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃; for 18.5h; Inert atmosphere;

DOI:10.1002/chem.202100877

Reference yield:

1,3,5-trimethyl-benzene (108-67-8) → bis(mesityl)ketene (87871-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tin (IV)-chloride

2: SOCl₂; pyridine; benzene

With pyridine; thionyl chloride; tin(IV) chloride; benzene;

DOI:10.1021/ja01219a010

upstream raw materials:

2,2-bis(2,4,6-trimethylphenyl)acetic acid

pyridine

thionyl chloride

benzene

Downstream raw materials:

α-Methyl-β,β-dimesitylethenol

trimesityl-vinyl alcohol

2,2-dimesityl-1-phenylethenol

1-(4-Chloro-phenyl)-2,2-bis-(2,4,6-trimethyl-phenyl)-ethenol

Refernces

• 1、 Roy, Avijit,Oestreich, Martin. "Metal-Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers". . p. 8273 - 8276. Retrieved 2021/05/11.
• 2、 Biali, Silvio E.,Rappoport, Zvi. "Stable Simple Enols. 3. Static and Dynamic NMR Behavior of Crowded Triarylethenols and Related Compounds. Three-Ring Flip as the Threshold Mechanism for Enantiomerization of Crowded Triarylvinyl Propellers". . p. 477 - 496. Retrieved 2007/10/02.