Pseudoisoeugenol

Base Information

• Chemical Name: Pseudoisoeugenol
• CAS No.: 98755-22-7
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• UNII: TQ75A9G9UX
• DSSTox Substance ID: DTXSID101337120
• Nikkaji Number: J460.240D,J498.742J
• Wikidata: Q76507392
• Wikipedia: Pseudoisoeugenol
• Mol file: 98755-22-7.mol

Synonyms:pseudoisoeugenol;trans-Pseudoisoeugenol;(E)-Pseudoisoeugenol;TQ75A9G9UX;UNII-TQ75A9G9UX;4-Methoxy-2-(1E)-1-propen-1-ylphenol;98755-22-7;Phenol, 4-methoxy-2-(1E)-1-propen-1-yl-;SCHEMBL7988046;DTXSID101337120;1-(e)-propenyl-2-hydroxy-5-methoxy benzene

Chemical Property of Pseudoisoeugenol

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 154

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Pseudoisoeugenol

There total 6 articles about Pseudoisoeugenol 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: 74.0%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + ethyltriphenylphosphonium bromide (1530-32-1) → (E)-4-methoxy-2-(prop-1-en-1-yl)phenol (98755-22-7)

Guidance literature:

ethyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 25 ℃; for 0.75h;

2-hydroxy-5-methoxybenzaldehyde; In tetrahydrofuran; hexane; for 3h;

DOI:10.1021/acs.joc.9b02263

Reference yield: 70.0%

2-allyl-4-methoxyphenol (584-82-7) → cis-4-methoxy-2-(1-propenyl)phenol (98755-19-2) + (E)-4-methoxy-2-(prop-1-en-1-yl)phenol (98755-22-7)

Guidance literature:

With potassium hydroxide; In methanol; at 160 ℃; for 1h;

DOI:10.1016/S0031-9422(98)00022-3

Reference yield:

allyl (4-methoxyphenyl) ether (13391-35-0) → (E)-4-methoxy-2-(prop-1-en-1-yl)phenol (98755-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / N,N-dimethyl-aniline / Heating

2: sodium tert-butoxide / dimethylsulfoxide / 12 h / 60 °C

With sodium t-butanolate; In dimethyl sulfoxide; N,N-dimethyl-aniline; 1: Claisen rearrangement;

DOI:10.1002/chem.200600332

upstream raw materials:

2-allyl-4-methoxyphenol

allyl (4-methoxyphenyl) ether

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde

Downstream raw materials:

Acetic acid 4-methoxy-2-((E)-propenyl)-phenyl ester

trans-pseudoisoeugenyl-2-methyl butyrate