2,4-dihydroxy-6-propyl-benzoic acid methyl ester

Base Information

• Chemical Name: 2,4-dihydroxy-6-propyl-benzoic acid methyl ester
• CAS No.: 55382-52-0
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• European Community (EC) Number: 810-694-4
• UNII: KAV9D8HC7J
• DSSTox Substance ID: DTXSID50451725
• Wikidata: Q82271901
• Metabolomics Workbench ID: 130805
• ChEMBL ID: CHEMBL3234668
• Mol file: 55382-52-0.mol

Synonyms:2,4-Dihydroxy-6-propyl-benzoesaeure-methylester;2,4-dihydroxy-6-propyl-benzoic acid methyl ester;Benzoic acid,2,4-dihydroxy-6-propyl-,methyl ester;2,4-dihydroxy-6-n-propylbenzoic acid,methyl ester;Methyl-Divoxinolcarboxylat;

Chemical Property of 2,4-dihydroxy-6-propyl-benzoic acid methyl ester

Chemical Property:

• Boiling Point: 388.6±27.0 °C(Predicted)
• PKA: 8.27±0.23(Predicted)
• PSA: 66.76000
• Density: 1.211±0.06 g/cm3(Predicted)
• LogP: 1.83690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 217

Purity/Quality:

97% purity ^*data from raw suppliers

Methyl2,4-dihydroxy-6-propylbenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=C(C(=CC(=C1)O)O)C(=O)OC
• Description: 2,4-dihydroxy-6-propyl-benzoic acid methyl ester is a carboxylate derivative and can be used as a pharmaceutical intermediate.
• Uses: Methyl Divarinolcarboxylate is used in methods of manufacturing Cannabidiol or Cannabidivarin.

Technology Process of 2,4-dihydroxy-6-propyl-benzoic acid methyl ester

There total 13 articles about 2,4-dihydroxy-6-propyl-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: 91.0%

methyl 3,5-dibromo-2,4-dihydroxy-6-propylbenzoate → 2,4-dihydroxy-6-n-propylbenzoic acid, methyl ester (55382-52-0)

Guidance literature:

With sodium hydroxide; Raney Ni/Al; at 0 ℃; for 3h;

Reference yield: 35.0%

1,1,1-trimethoxybutane (43083-12-1) + 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (102342-54-1) → 2,4-dihydroxy-6-n-propylbenzoic acid, methyl ester (55382-52-0)

Guidance literature:

With titanium tetrachloride; In dichloromethane; 1.) -78 deg C, 2-3 h, 2.) RT, overnight;

DOI:10.1021/jo00363a004

Reference yield: 23.0%

1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (102342-54-1) + butyryl chloride (141-75-3) → 2,4-dihydroxy-6-n-propylbenzoic acid, methyl ester (55382-52-0)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; 1.) -78 deg C, 2-3 h, 2.) RT, overnight;

DOI:10.1021/jo00363a004

upstream raw materials:

diazomethane

2,4-dihydroxy-6-propylbenzoic acid

4-methyleneoxetan-2-one

methyl 3-oxohexanoate

Downstream raw materials:

methyl 2-hydroxy-4-methoxy-6-(n-propyl)benzoate

5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-7-propyl-2H-chromene-6-carboxylic acid methyl ester

CBDVA-Methylester

tetrahydrocannabivarin

Refernces

• 1、 -. "SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP". Page/Page column 17. . Retrieved 2019/03/05.
• 2、 Mori, Kenji,Kamada, Atsushi,Mori, Hideto. "Synthetic Microbial Chemistry, XXI. Synthesis of Differanisole A, an Inducer of Differentiation". . p. 303 - 306. Retrieved 2007/10/02.