beta-Ethenyl-4-fluorobenzenepropanoic acid

Base Information

• Chemical Name: beta-Ethenyl-4-fluorobenzenepropanoic acid
• CAS No.: 1423027-07-9
• Molecular Formula: C₁₁H₁₁FO₂
• Molecular Weight: 194.206
• DSSTox Substance ID: DTXSID501279809
• Mol file: 1423027-07-9.mol

Synonyms:DTXSID501279809;1423027-07-9;beta-Ethenyl-4-fluorobenzenepropanoic acid

Chemical Property of beta-Ethenyl-4-fluorobenzenepropanoic acid

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.07430775
• Heavy Atom Count: 14
• Complexity: 207

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of beta-Ethenyl-4-fluorobenzenepropanoic acid

There total 4 articles about beta-Ethenyl-4-fluorobenzenepropanoic 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: 93.0%

Triethyl orthoacetate (78-39-7) + (E)-3-(4-fluorophenyl)-2-propen-1-ol (124980-95-6) → 3-(4-fluorophenyl)pent-4-enoic acid (1423027-07-9,918149-75-4)

Guidance literature:

Triethyl orthoacetate; (E)-3-(4-fluorophenyl)-2-propen-1-ol; With phenol; at 160 ℃; for 16h; Dean-Stark;

With sodium hydroxide; In methanol; water; at 100 ℃; for 1h; Dean-Stark;

DOI:10.1021/acs.orglett.8b00996

Reference yield: 85.0%

3-(4-fluorophenyl)prop-2-en-1-ol (124980-95-6,7361-55-9) + Triethyl orthoacetate (78-39-7) → 3-(4-fluorophenyl)pent-4-enoic acid (1423027-07-9,918149-75-4)

Guidance literature:

With hexanoic acid; In ethanol; at 70 - 150 ℃; Reflux;

DOI:10.1039/c3ob27321k

Reference yield:

ethyl 4-fluorocinnamate (136265-10-6,352-03-4,24393-50-8) → 3-(4-fluorophenyl)pent-4-enoic acid (1423027-07-9,918149-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene / 3.25 h / -78 - 25 °C / Inert atmosphere

2.1: phenol / 16 h / 160 °C / Dean-Stark

2.2: 1 h / 100 °C / Dean-Stark

With diisobutylaluminium hydride; phenol; In toluene;

DOI:10.1021/acs.orglett.8b00996

upstream raw materials:

3-(4-fluorophenyl)prop-2-en-1-ol

Triethyl orthoacetate

(E)-3-(4-fluorophenyl)-2-propen-1-ol

4-fluorobenzaldehyde

Downstream raw materials:

(4S,5R)-4-(4-fluorophenyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one

(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol