Ethyl 4-methyl-3-pentenoate

Base Information

• Chemical Name: Ethyl 4-methyl-3-pentenoate
• CAS No.: 6849-18-9
• Molecular Formula: C8H14 O2
• Molecular Weight: 142.198
• Hs Code.: 2916190090
• European Community (EC) Number: 614-536-3
• UNII: 6LO1L4F1TE
• DSSTox Substance ID: DTXSID20218600
• Nikkaji Number: J3.473.120I
• Wikidata: Q27265112
• Mol file: 6849-18-9.mol

Synonyms:Ethyl 4-methyl-3-pentenoate;6849-18-9;ethyl 4-methylpent-3-enoate;3-Pentenoic acid, 4-methyl-, ethyl ester;UNII-6LO1L4F1TE;6LO1L4F1TE;SCHEMBL8465901;DTXSID20218600;YBUMUFVIEWSXLA-UHFFFAOYSA-N;4-Methyl-3-pentenoic acid ethyl ester;4-methyl-pent-3-enoic acid ethyl ester;3-pentenoic acid ,4-methyl-,ethyl ester;Q27265112

Chemical Property of Ethyl 4-methyl-3-pentenoate

Chemical Property:

• Vapor Pressure: 1.63mmHg at 25°C
• Melting Point: -65.52°C (estimate)
• Refractive Index: 1.4329
• Boiling Point: 168.3°C at 760 mmHg
• Flash Point: 63°C
• PSA: 26.30000
• Density: 0.902g/cm³
• LogP: 1.90580
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 132

Purity/Quality:

99.0.% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC=C(C)C

Technology Process of Ethyl 4-methyl-3-pentenoate

There total 18 articles about Ethyl 4-methyl-3-pentenoate 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: 88.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + isoprene (78-79-5,9003-31-0) → ethyl 4-methyl-3-pentenoate (6849-18-9)

Guidance literature:

With dichloro(1,5-cyclooctadiene)palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100 ℃; for 20h; under 30003 - 67506.8 Torr; Inert atmosphere; Autoclave;

DOI:10.1002/anie.201404563

Reference yield: 73.0%

ethyl-4-methyl-2-(E)-penteneoate (15790-86-0) → ethyl 4-methyl-3-pentenoate (6849-18-9)

Guidance literature:

With diethylamine; In dichloromethane; at 0 ℃; Irradiation;

DOI:10.1016/S0040-4020(01)85681-7

Reference yield:

ethanol (64-17-5) + carbon monoxide (201230-82-2) + isoprene (78-79-5,9003-31-0) → dihydro-5,5-dimethyl-2(3H)-furanone (3123-97-5) + ethyl 4-methyl-3-pentenoate (6849-18-9) + ethyl 4-methyl-4-pentenoate (4911-54-0) + 3-Methyl-hexen-3-disaeure-diethylester (39155-12-9)

Guidance literature:

Multistep reaction. Further byproducts given; (i) PdCl₂, (ii) /BRN= 3587209/, EtOH;

DOI:10.1021/ja01096a010

upstream raw materials:

ethanol

4-methyl-pent-3-enoic acid

4-methyl-2-pentenoyl chloride

chloroformic acid ethyl ester

Downstream raw materials:

dihydro-5,5-dimethyl-2(3H)-furanone

4-methyl-pent-3-enoic acid

1-bromo-4-methylpent-3-ene

(2E)-but-2-enedioic acid

Refernces

• 1、 Fang, Xianjie,Li, Haoquan,Jackstell, Ralf,Beller, Matthias. "Palladium-catalyzed alkoxycarbonylation of conjugated dienes under acid-free conditions: Atom-economic synthesis of β,γ-unsaturated esters". supporting information. p. 9030 - 9034. Retrieved 2014/09/17.
• 2、 Cho, In Sik,Alper, Howard. "Selective hydrogenation of simple and functionalized conjugated dienes using a binuclear palladium complex catalyst precursor". . p. 5673 - 5676. Retrieved 2007/10/02.