methyl (E)-2-phenyl-2-octenoate

Base Information

• Chemical Name: methyl (E)-2-phenyl-2-octenoate
• CAS No.: 100340-47-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 100340-47-4.mol

Synonyms:methyl (E)-2-phenyl-2-octenoate

Chemical Property of methyl (E)-2-phenyl-2-octenoate

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-2-phenyl-2-octenoate

There total 11 articles about methyl (E)-2-phenyl-2-octenoate 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: 48.6%

iodobenzene (591-50-4) + (Z)/(E)(1-methoxycarbonyl-1-heptenyl)zinc iodide → methyl (E)-2-phenyl-2-octenoate (100340-47-4) + methyl (Z)-2-phenyl-2-octenoate (100340-48-5)

Guidance literature:

With triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/0022-328X(93)83005-G

Reference yield:

methyl (E)-2-tributylstannyl-2-octenoate (144079-75-4,145099-81-6) → methyl (E)-2-phenyl-2-octenoate (100340-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) I₂, 2.) aq. KF / 1.) CH₂Cl₂, 20 deg C, 2.) Et₂O, 20 deg C

2: 2.) aq. NH₄Cl / Pd(PPh₃)4 / tetrahydrofuran / 1.) -20 to 20 deg C

With potassium fluoride; iodine; ammonium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)60119-3

Reference yield:

phenylzinc chloride (28557-00-8) + methyl (E)-2-iodo-2-octenoate (144079-78-7) → methyl (E)-2-phenyl-2-octenoate (100340-47-4) + methyl (Z)-2-phenyl-2-octenoate (100340-48-5)

Guidance literature:

With ammonium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) -20 to 20 deg C;

DOI:10.1016/S0040-4039(00)60119-3

upstream raw materials:

iodobenzene

phenylzinc chloride

methyl (E)-2-iodo-2-octenoate

methanol

Refernces

• 1、 Rossi, Renzo,Carpita, Adriano,Bellina, Fabio,Cossi, Paolo. "Palladium-catalyzed reaction between aryl or alkenyl halides and (1-carbalkoxy-1-alkenyl)zinc iodides. A new class of unmasked β-substituted acrylate α-anion equivalents". . p. 33 - 43. Retrieved 2007/10/02.
• 2、 Rousseau, G.,Slougui, N.. "ETUDE DE LA REACTION CHLOROCARBENE-ACETALS DE CETENES. II. STEREOSELECTIVITE DE LA REACTION.". . p. 2653 - 2664. Retrieved 2007/10/02.