Benzenepropanoic acid, a-(3-iodo-2-propenyl)-, methyl ester, (Z)-

Base Information

• Chemical Name: Benzenepropanoic acid, a-(3-iodo-2-propenyl)-, methyl ester, (Z)-
• CAS No.: 138536-59-1
• Molecular Formula: C₁₃H₁₅IO₂
• Molecular Weight: 330.165
• Mol file: 138536-59-1.mol

Synonyms:

Chemical Property of Benzenepropanoic acid, a-(3-iodo-2-propenyl)-, methyl ester, (Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenepropanoic acid, a-(3-iodo-2-propenyl)-, methyl ester, (Z)-

There total 2 articles about Benzenepropanoic acid, a-(3-iodo-2-propenyl)-, methyl ester, (Z)- 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: 50.0%

methyl (E)-2-benzyl-5-trimethylsilyl-4-pentenoate (154194-01-1) → methyl (Z)-2-benzyl-5-iodo-4-pentenoate (138536-59-1)

Guidance literature:

With iodine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0022-328X(94)87005-5

Reference yield:

2-Benzyl-2-((E)-3-trimethylsilanyl-allyl)-malonic acid dimethyl ester → methyl (Z)-2-benzyl-5-iodo-4-pentenoate (138536-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / LiCl / hexamethylphosphoric acid triamide / 24 h / 120 °C

2: 50 percent / I₂ / CH₂Cl₂ / 1 h / Ambient temperature

With iodine; lithium chloride; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0022-328X(94)87005-5

Reference yield: 50.0%

trimethylsilyltributyltin (17955-46-3) + methyl (Z)-2-benzyl-5-iodo-4-pentenoate (138536-59-1) → (C4H9)3SnC5H6(O)CH2C6H5 (154194-07-7)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In N,N-dimethyl-formamide; byproducts: methyl 2-benzyl-4-pentenoate; (Ar); solvent contained a trace of water; stirring at room temp. for 15 h; 10% NH4OH added to soln.; mixt. extd. with ethyl acetate; org. layer washed with 10% HCl, brine, satd. NaHCO3, and brine, dried over Na2SO4 and concd.; residue chromd. (silica gel, hexane/ethyl acetate); elem. anal.; mol. mass detd. by mass spectrometry;

DOI:10.1016/0022-328X(94)87005-5

upstream raw materials:

methyl (E)-2-benzyl-5-trimethylsilyl-4-pentenoate

Downstream raw materials:

methyl 2-allyl-3-phenylpropionate

(C₄H₉)3SnC₅H₆(O)CH₂C₆H₅