Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester
• CAS No.: 117390-08-6
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214
• DSSTox Substance ID: DTXSID101243806
• Nikkaji Number: J763.137E
• Mol file: 117390-08-6.mol

Synonyms:117390-08-6;Methyl 4-(3-hydroxyprop-1-en-1-yl)benzoate;Benzoic acid, 4-[(1E)-3-hydroxy-1-propen-1-yl]-, methyl ester;87808-23-9;SCHEMBL5071212;Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester;DTXSID101243806;CS-0347233;EN300-1828846;4-(3-Hydroxy-1-propenyl)benzoic acid methyl ester;Methyl 4-[(1E)-3-hydroxy-1-propen-1-yl]benzoate

Chemical Property of Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C=CCO
• Isomeric SMILES: COC(=O)C1=CC=C(C=C1)/C=C/CO

Technology Process of Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester

There total 10 articles about Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester 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:

4-((E)-3-oxoprop-1-enyl)-benzoic acid methyl ester (73166-52-6,78024-60-9) → 4-[(1E)-3-hydroxy-1-propen-1-yl]benzoic acid methyl ester (87808-23-9,117390-08-6)

Guidance literature:

With sodium tetrahydroborate; In methanol;

Reference yield:

methyl 4-iodobenzoate (619-44-3) + allyl alcohol (107-18-6) → 4-[(1E)-3-hydroxy-1-propen-1-yl]benzoic acid methyl ester (87808-23-9,117390-08-6)

Guidance literature:

With silver(I) acetate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jacs.0c00147

Reference yield:

methyl 4-formylbenzoate (1571-08-0) → 4-[(1E)-3-hydroxy-1-propen-1-yl]benzoic acid methyl ester (87808-23-9,117390-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / piperidine, pyridine / 1.) 60 deg C, 1 h, 2.) 100 deg C, 2 h

2: 1.) triethylamine, diethyl chlorophosphate, 2.) NaBH₄ / 1.) THF, room temperature, 3 h, 2.) THF, 2 h, room temperature

With piperidine; pyridine; sodium tetrahydroborate; diethyl chlorophosphate; triethylamine;

upstream raw materials:

(E)-4-(methoxycarbonyl)cinnamic acid

methanol

4-iodobenzoic acid

trimethyl([[(2E)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy])silane

Downstream raw materials:

methyl (E)-4-(3-chloroprop-1-en-1-yl)benzoate