alpha-(Acetyloxy)benzeneacetaldehyde

Base Information

• Chemical Name: alpha-(Acetyloxy)benzeneacetaldehyde
• CAS No.: 22094-21-9
• Molecular Formula: C10H10O3
• Molecular Weight: 178.188
• DSSTox Substance ID: DTXSID201301996
• Nikkaji Number: J2.187.007B
• Mol file: 22094-21-9.mol

Synonyms:SCHEMBL11118451;DTXSID201301996;alpha-(Acetyloxy)benzeneacetaldehyde;22094-21-9

Chemical Property of alpha-(Acetyloxy)benzeneacetaldehyde

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC(C=O)C1=CC=CC=C1

Technology Process of alpha-(Acetyloxy)benzeneacetaldehyde

There total 10 articles about alpha-(Acetyloxy)benzeneacetaldehyde 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: 87.0%

2,3-epoxy-3-phenyl-1-propanol (21915-53-7,40641-81-4,91465-28-0,98819-67-1,98819-68-2,99528-63-9,104196-23-8,105663-44-3,116661-35-9) + lead(IV) tetraacetate (546-67-8) → 2-acetoxy-2-phenylacetaldehyde (22094-21-9)

Guidance literature:

In benzene; at 50 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.056

Reference yield: 86.0%

acetic acid dodecylsulfanylcarbonyl-phenyl-methyl ester → 2-acetoxy-2-phenylacetaldehyde (22094-21-9)

Guidance literature:

With triethylsilane; palladium on activated charcoal; In acetone; at 20 ℃; for 1h;

DOI:10.1055/s-2004-815427

Reference yield: 84.0%

Acetic acid ethylsulfanylcarbonyl-phenyl-methyl ester (82027-42-7) → 2-acetoxy-2-phenylacetaldehyde (22094-21-9)

Guidance literature:

With triethylsilane; palladium on activated charcoal; In acetone; Ambient temperature;

DOI:10.1021/ja00175a043

upstream raw materials:

2-acetoxy-2-phenylacetyl chloride

cyano(phenyl)methyl acetate

Acetic acid ethylsulfanylcarbonyl-phenyl-methyl ester

Acetic acid 2-methoxy-1-phenyl-2-phenylsulfanyl-ethyl ester

Downstream raw materials:

2-(1'-Acetoxybenzyl)-3-phenyl-1,3-oxazolidin

(3E)-5-acetoxy-5-phenylpent-3-en-2-one

(2E)-4-acetoxy-1,4-diphenylbut-2-en-1-one

(R)-1-phenyl-1,2-ethanediol

Refernces

• 1、 Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Mu?oz, Pedro E.,Jimenez, Fermín,Bouanou, Hanane. "Lead(IV) acetate mediated cleavage of β-hydroxy ethers: Enantioselective synthesis of α-acetoxy carbonyl compounds". experimental part. p. 8910 - 8917. Retrieved 2011/12/01.
• 2、 Wang, Libo,Nakamura, Shuichi,Toru, Takeshi. "Highly enantioselective reaction of lithiated N-Boc-thiazolidine: A new chiral formyl anion equivalent". . p. 2168 - 2169. Retrieved 2007/10/03.