4-Hexenoic acid, 4-methyl-3-oxo-, ethyl ester

Base Information

• Chemical Name: 4-Hexenoic acid, 4-methyl-3-oxo-, ethyl ester
• CAS No.: 27761-56-4
• Molecular Formula: C9H14O3
• Molecular Weight: 170.21
• Mol file: 27761-56-4.mol

Synonyms:

Chemical Property of 4-Hexenoic acid, 4-methyl-3-oxo-, ethyl ester

Chemical Property:

• Boiling Point: 240℃
• Flash Point: 98℃
• Density: 0.994

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Hexenoic acid, 4-methyl-3-oxo-, ethyl ester

There total 4 articles about 4-Hexenoic acid, 4-methyl-3-oxo-, ethyl ester 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: 68.0%

(E)-2-methylbut-2-enoyl chloride (35660-94-7) + Ethyl trimethylsilyl malonate (18457-03-9) → ethyl trans-4-methyl-3-oxo-4-hexenoate (25654-10-8,27761-56-4)

Guidance literature:

With n-butyllithium; In 1,2-dimethoxyethane; diethyl ether; hexane; at -78 ℃; for 1h; warmed up to O deg C over 20 min.,;

DOI:10.1002/jhet.5570180227

Reference yield:

(E)-2-methylbut-2-enoyl chloride (35660-94-7) + ethyl acetate (141-78-6) → ethyl (E)-4-methyl-3-oxo-4-hexenoate (25654-10-8,27761-56-4)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 20 min, 2.) -70 deg C, 2 h;

DOI:10.1016/0040-4039(91)80577-S

Reference yield:

2,5,6-Trimethyl-4-oxo-5,6-dihydro-4H-pyran-3-carboxylic acid ethyl ester → ethyl (E)-4-methyl-3-oxo-4-hexenoate (25654-10-8,27761-56-4)

Guidance literature:

Multistep reaction; (i) aq. NaOH, (ii) K₂CO₃, (heating under reduced pressure);

upstream raw materials:

(E)-2-methylbut-2-enoyl chloride

ethyl acetate

Ethyl trimethylsilyl malonate

Downstream raw materials:

nectriapyrone

(E)-5-(1-methyl-1-propenyl)-1-phenylpyrazole

5,6-Dimethyl-4-oxo-1-phenylamino-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester

Refernces

• 1、 Abramson,Wormser. "Synthesis of nectriapyrone". . p. 363 - 366. Retrieved 2007/10/02.