Atropaldehyde diethyl acetal

Base Information

• Chemical Name: Atropaldehyde diethyl acetal
• CAS No.: 80234-04-4
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• DSSTox Substance ID: DTXSID70462994
• Wikidata: Q82287686
• Mol file: 80234-04-4.mol

Synonyms:atropaldehyde diethyl acetal;80234-04-4;2-phenylpropenal diethyl acetal;SCHEMBL8934663;(1-Diethoxymethyl-vinyl)benzene;[1-(diethoxymethyl)vinyl]benzene;DTXSID70462994;PGRGWTSTROMQAI-UHFFFAOYSA-N;1-(diethoxy-methyl)-vinyl-benzene;ethyl2,4-dichloro-6-methylnicotinate

Chemical Property of Atropaldehyde diethyl acetal

Chemical Property:

• PSA: 18.46000
• LogP: 3.09890
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 206.130679813
• Heavy Atom Count: 15
• Complexity: 177

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(C(=C)C1=CC=CC=C1)OCC

Technology Process of Atropaldehyde diethyl acetal

There total 12 articles about Atropaldehyde diethyl acetal 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: 86.0%

ethanol (64-17-5) + 1,1-dichloro-2-phenylcyclopropane (2415-80-7) → 2-phenylacrylaldehyde diethyl acetal (80234-04-4)

Guidance literature:

With sodium hydroxide; for 24h; Reflux;

DOI:10.1021/acs.orglett.7b00558

Reference yield: 84.0%

2-bromo-3,3-diethoxypropene (17592-40-4) + phenylboronic acid (98-80-6) → 2-phenylacrylaldehyde diethyl acetal (80234-04-4)

Guidance literature:

With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 40 ℃; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1055/a-1322-3916

Reference yield: 84.0%

2-bromo-3,3-diethoxypropene (17592-40-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2-phenylacrylaldehyde diethyl acetal (80234-04-4)

Guidance literature:

With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 40 ℃; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1055/a-1322-3916

upstream raw materials:

ethanol

1-ethoxy-2-phenylcyclopropene

orthoformic acid triethyl ester

1,1-dichloro-2-phenylcyclopropane

Downstream raw materials:

phenylpropionaldehyde diethyl acetal

2,2-diethoxyacetophenone

phenyl-2 naphto<2,1-b>furanne

Refernces

• 1、 Zhang, Li. "Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes". supporting information. p. 723 - 727. Retrieved 2021/02/26.
• 2、 Song, Qing-Wen,Yu, Bing,Liu, An-Hua,He, Ying,Yang, Zhen-Zhen,Diao, Zhen-Feng,Song, Qing-Chuan,Li, Xue-Dong,He, Liang-Nian. "PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene". . p. 19009 - 19014. Retrieved 2013/10/22.