3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid methyl ester

Base Information

• Chemical Name: 3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid methyl ester
• CAS No.: 135743-14-5
• Molecular Formula: C₂₃H₃₂O₃
• Molecular Weight: 356.505
• DSSTox Substance ID: DTXSID501121949
• Nikkaji Number: J412.506A
• Mol file: 135743-14-5.mol

Synonyms:3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid methyl ester;135743-14-5;methyl 3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-hydroxy-5-(3-methylbut-2-enyl)benzoate;DTXSID501121949;Methyl 3-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoate;Methyl 3-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-4-hydroxy-5-(3-methyl-2-buten-1-yl)benzoate

Chemical Property of 3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid methyl ester

Chemical Property:

• XLogP3: 7.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 356.23514488
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C(=O)OC)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC1=CC(=CC(=C1O)CC=C(C)C)C(=O)OC)/C)C

Technology Process of 3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid methyl ester

There total 2 articles about 3-[(2E)-3,7-Dimethyl-2,6-octadienyl]-4-hydroxy-5-(3-methyl-2-butenyl)benzoic acid 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: 84.0%

trans-geranyl bromide (6138-90-5) + methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate (101511-34-6) → methyl (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoate (135743-14-5)

Guidance literature:

methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate; With sodium hydride; In mineral oil; at 50 ℃; for 1h;

trans-geranyl bromide; In mineral oil; at 40 ℃; for 24h;

DOI:10.1080/00397911.2017.1288823

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid (135743-12-3) → methyl (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoate (135743-14-5) + 3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-methoxy-5-(3-methyl-but-2-enyl)-benzoic acid methyl ester

Guidance literature:

In methanol; diethyl ether; at 4 ℃;

DOI:10.1271/bbb.63.1650

Reference yield: 95.0%

methyl (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoate (135743-14-5) → (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid (135743-12-3)

Guidance literature:

With potassium hydroxide; In 1,1,1-trideuteromethanol; water; for 3h; Reflux;

DOI:10.1080/00397911.2017.1288823

upstream raw materials:

diazomethane

(E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid

trans-geranyl bromide

methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate

Downstream raw materials:

4-Acetoxy-3-((E)-3,7-dimethyl-octa-2,6-dienyl)-5-(3-methyl-but-2-enyl)-benzoic acid methyl ester

(E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-hydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid