Vinyl cinnamic acid

Base Information

• Chemical Name: Vinyl cinnamic acid
• CAS No.: 91344-46-6
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.199
• DSSTox Substance ID: DTXSID901292421
• Mol file: 91344-46-6.mol

Synonyms:vinyl cinnamic acid;SCHEMBL175544;DTXSID901292421;2-(Phenylmethylene)-3-butenoic acid;91344-46-6

Chemical Property of Vinyl cinnamic acid

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC(=CC1=CC=CC=C1)C(=O)O

Technology Process of Vinyl cinnamic acid

There total 5 articles about Vinyl cinnamic acid 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: 60.0%

carbon monoxide (201230-82-2) + [(1Z)-2-bromobuta-1,3-dien-1-yl]benzene (24182-36-3) → 2-[1-Phenyl-meth-(Z)-ylidene]-but-3-enoic acid (67946-44-5,91344-46-6) + 5-Methyl-4-[1-phenyl-meth-(Z)-ylidene]-dihydro-furan-2,3-dione (125101-18-0)

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; nickel cyanide; In toluene; at 80 ℃; under 735.5 Torr; Mechanism;

DOI:10.1016/S0040-4039(00)99079-8

Reference yield:

1-ethoxy-3-hydroxy-1-butyne (36677-86-8) + benzaldehyde (100-52-7) → 2-benzylidene-but-3-enoic acid (91344-46-6)

Guidance literature:

With diethyl ether; ethylmagnesium bromide; Erwaermen des Reaktionsprodukts mit aethanol. KOH;

Reference yield:

Ethyl (E/Z)-2-bromobut-2-enoate (59065-89-3) + benzaldehyde (100-52-7) → 2-benzylidene-but-3-enoic acid (91344-46-6)

Guidance literature:

Multistep reaction; (i) Mg, HgCl₂, THF, benzene, (ii) TsOH, benzene, (iii) KOH, EtOH;

upstream raw materials:

crotonic anhydride

benzaldehyde

triethylamine

1-ethoxy-3-hydroxy-1-butyne

Downstream raw materials:

1-(phenylmethyl)butanoic acid

2-benzyl-crotonic acid

rac-2-benzyl-3-butenoic acid

methyl (E)-2-benzylidenebut-3-enoate

Refernces