4-Ketododecanoic acid methyl ester

Base Information

• Chemical Name: 4-Ketododecanoic acid methyl ester
• CAS No.: 33566-59-5
• Molecular Formula: C13H24O3
• Molecular Weight: 228.332
• Mol file: 33566-59-5.mol

Synonyms:4-Oxododecansaeuremethylester;Dodecanoic acid,4-oxo-,methyl ester;methyl 4-oxo-dodecanoate;4-Ketododecanoic acid methyl ester;Methyl-4-oxo-laurat;4-Ketolaurinsaeuremethylester;

Chemical Property of 4-Ketododecanoic acid methyl ester

Chemical Property:

• PSA: 43.37000
• LogP: 3.25930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Ketododecanoic acid methyl ester

There total 16 articles about 4-Ketododecanoic acid methyl 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: 73.0%

methanol (67-56-1) + 2-methyl-2-tetradecen-6-one → methyl 4-oxo-dodecanoate (33566-59-5)

Guidance literature:

With sodium hydroxide; ozone; In dichloromethane; at -70 ℃;

DOI:10.1080/00397919408011738

Reference yield: 62.0%

1-Iodooctane (629-27-6) + carbon monoxide (201230-82-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-oxo-dodecanoate (33566-59-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tetrabutylammonium (cyano)trihydroborate; In methanol; at 80 ℃; for 19h; under 69164.6 Torr; Autoclave;

DOI:10.1021/ol7031043

Reference yield:

heptanal (111-71-7) → methyl 4-oxo-dodecanoate (33566-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / dimethylformamide / 48 h / Heating

2: H₂ / Pd/C

With hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1021/jo00149a033

upstream raw materials:

C₁₉H₃₆S₅

ethanol

n-octyl-magnesium iodide

succinic acid monomethylester chloride

Downstream raw materials:

4-oxododecanoic acid

(R)-4-dodecanolide

5(S)-octyl-2(3H)-dihydrofuranone

5-heptyldihydro-2(3H)-furanone

Refernces

• 1、 Kawamoto, Takuji,Uehara, Shohei,Hirao, Hidefumi,Fukuyama, Takahide,Matsubara, Hiroshi,Ryu, Ilhyong. "Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes". . p. 3999 - 4007. Retrieved 2014/05/20.
• 2、 Benincori, Tiziana,Rizzo, Simona,Pilati, Tullio,Ponti, Alessandro,Sada, Mara,Pagliarini, Ella,Ratti, Simona,Giuseppe, Celentano,De Ferra, Lorenzo,Sannicolo, Franco. "Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes". . p. 2289 - 2297. Retrieved 2007/10/03.