Ethyl 3-(acetoxy)crotonate

Base Information

• Chemical Name: Ethyl 3-(acetoxy)crotonate
• CAS No.: 26805-39-0
• Molecular Formula: C8H12 O4
• Molecular Weight: 172.181
• European Community (EC) Number: 249-519-6,248-635-4,248-011-1
• NSC Number: 167587
• DSSTox Substance ID: DTXSID501229266
• Nikkaji Number: J249.050A,J250.804D
• Mol file: 26805-39-0.mol

Synonyms:Ethyl 3-(acetoxy)crotonate;ethyl (Z)-3-acetyloxybut-2-enoate;29214-62-8;26805-39-0;2-Butenoic acid, 3-(acetyloxy)-, ethyl ester, (Z)-;SCHEMBL11126166;3-Acetoxycrotonic acid ethyl ester;DTXSID501229266;NSC167587;3-Acetoxy-2-butenoic acid ethyl ester;NSC-167587

Chemical Property of Ethyl 3-(acetoxy)crotonate

Chemical Property:

• Vapor Pressure: 0.148mmHg at 25°C
• Boiling Point: 215.4°Cat760mmHg
• Flash Point: 98.6°C
• PSA: 52.60000
• Density: 1.069g/cm³
• LogP: 1.01640
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 205

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)OC(=O)C
• Isomeric SMILES: CCOC(=O)/C=C(/C)\OC(=O)C

Technology Process of Ethyl 3-(acetoxy)crotonate

There total 6 articles about Ethyl 3-(acetoxy)crotonate 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: 55.0%

Isopropenyl acetate (108-22-5) + ethyl acetoacetate (141-97-9) → (Z)-ethyl 3-acetoxybut-2-enoate (26805-39-0)

Guidance literature:

With toluene-4-sulfonic acid; at 130 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jacs.9b08586

Reference yield:

ethyl acetoacetate (141-97-9) + acetyl chloride (75-36-5) → (Z)-ethyl 3-acetoxybut-2-enoate (26805-39-0) + ethyl-β-acetoxycrotonate (27750-19-2)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1021/ja00329a051

Reference yield:

ketene diethyl acetal (2678-54-8) + acetyl chloride (75-36-5) → (Z)-ethyl 3-acetoxybut-2-enoate (26805-39-0) + ethyl (Z)-3-ethoxybut-2-enoate (5331-73-7) + ethyl acetoacetate (141-97-9) + ethyl acetate (141-78-6)

Guidance literature:

at 50 - 55 ℃;

DOI:10.1021/ja01254a015

upstream raw materials:

ethyl acetoacetate

acetyl chloride

ketene diethyl acetal

Isopropenyl acetate

Downstream raw materials:

ethyl 3-methylbut-2-enoate

ethyl acetoacetate

Acetyl bromide

acetylacetone

Refernces

• 1、 Li, Jie,Ren, Qianyi,Cheng, Xinyi,Karaghiosoff, Konstantin,Knochel, Paul. "Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents". supporting information. p. 18127 - 18135. Retrieved 2019/11/19.