Methyl 12-oxo-12-phenyldodecanoate

Base Information

• Chemical Name: Methyl 12-oxo-12-phenyldodecanoate
• CAS No.: 104828-35-5
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• Hs Code.: 2918300090
• NSC Number: 132295
• DSSTox Substance ID: DTXSID40299719
• Wikidata: Q82042250
• Mol file: 104828-35-5.mol

Synonyms:methyl 12-oxo-12-phenyldodecanoate;104828-35-5;NSC132295;DTXSID40299719;methyl12-oxo-12-phenyldodecanoate;AKOS015949368;CS-W001284;NSC-132295;s11675;MS-20914;FT-0685068;W-204538

Chemical Property of Methyl 12-oxo-12-phenyldodecanoate

Chemical Property:

• PSA: 43.37000
• LogP: 4.94330
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 306

Purity/Quality:

98%min ^*data from raw suppliers

Methyl12-Oxo-12-phenyldodecanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CCCCCCCCCCC(=O)C1=CC=CC=C1
• Uses: Methyl 12-Oxo-12-phenyldodecanoate is used as a reactant in the synthesis of fatty acid analogs and phospholipids with aromatic fatty acid chains.

Technology Process of Methyl 12-oxo-12-phenyldodecanoate

There total 2 articles about Methyl 12-oxo-12-phenyldodecanoate 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: 74.0%

iodobenzene (591-50-4) + carbon monoxide (201230-82-2) + B-(10-carbomethoxydecyl)-9-borabicyclo{3.3.1}nonane (104828-34-4) → 12-Oxo-12-phenyl-dodecanoic acid methyl ester (104828-35-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; zinc(II) acetylacetonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 50 - 55 ℃; for 24h; under 760 Torr;

DOI:10.1016/0022-328X(86)80017-1

Reference yield:

11-chlorocarbonyl-undecanoic acid methyl ester (4082-57-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 12-Oxo-12-phenyl-dodecanoic acid methyl ester (104828-35-5)

Guidance literature:

With aluminium trichloride; at 4 - 20 ℃; for 13h;

DOI:10.1016/S0040-4039(02)00758-X

Reference yield:

12-Oxo-12-phenyl-dodecanoic acid methyl ester (104828-35-5) → 12-Phenyldodecanoic Acid (14507-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. HCl

2.1: NH₂NH₂; KOH / ethane-1,2-diol / 4 h / Heating

2.2: 70 percent / H₃O(+) / H₂O

With hydrogenchloride; potassium hydroxide; hydrazine; In ethylene glycol; 2.1: Huang-Minlon reaction;

DOI:10.1016/S0040-4039(02)00758-X

upstream raw materials:

iodobenzene

carbon monoxide

B-(10-carbomethoxydecyl)-9-borabicyclo{3.3.1}nonane

11-chlorocarbonyl-undecanoic acid methyl ester

Downstream raw materials:

12-oxo-12-phenyldodecanoic acid

12-Phenyldodecanoic Acid

C₃₆H₅₄O₃

Refernces

• 1、 Wakita, Yoshiaki,Yasunaga, Tomoyuki,Akita, Masahiro,Kojima, Masaharu. "PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING OF ORGANOBORANES WITH ARYL IODIDES OR BENZYL HALIDES IN THE PRESENCE OF BIS(ACETYLACETONATO)ZINC (II)". . p. C17 - C20. Retrieved 2007/10/02.