2-Hydroxy-3,6-dimethoxybenzaldehyde

Base Information

• Chemical Name: 2-Hydroxy-3,6-dimethoxybenzaldehyde
• CAS No.: 64466-51-9
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 2912499000
• DSSTox Substance ID: DTXSID90428279
• Nikkaji Number: J1.367.651H
• Mol file: 64466-51-9.mol

Synonyms:2-hydroxy-3,6-dimethoxybenzaldehyde;64466-51-9;2-Hydroxy-3,6-dimethoxy-benzaldehyde;SCHEMBL2750347;DTXSID90428279;TVMMXJBGOHHJBA-UHFFFAOYSA-N;AKOS006272814;CS-0250437;EN300-5086940;Z3227034404

Chemical Property of 2-Hydroxy-3,6-dimethoxybenzaldehyde

Chemical Property:

• PSA: 55.76000
• LogP: 1.22190
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxy-3,6-dimethoxybenzaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)OC)O)C=O

Technology Process of 2-Hydroxy-3,6-dimethoxybenzaldehyde

There total 15 articles about 2-Hydroxy-3,6-dimethoxybenzaldehyde 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: 96.0%

3,6-dimethoxy-2-(methoxymethoxy)benzaldehyde (211935-28-3) → 3,6-Dimethoxy-2-hydroxybenzaldehyde (64466-51-9)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; water; at 55 ℃;

DOI:10.1016/S0040-4039(98)01046-6

Reference yield:

6-bromo-2-hydroxy-3-methoxybenzaldehyde (20035-41-0) + sodium methylate (124-41-4) → 3,6-Dimethoxy-2-hydroxybenzaldehyde (64466-51-9)

Guidance literature:

With copper(l) iodide; In methanol; N,N-dimethyl-formamide; for 4h; Heating;

Reference yield:

2,5-dimethoxyphenol (18113-18-3) → 3,6-Dimethoxy-2-hydroxybenzaldehyde (64466-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: n-BuLi; TMEDA / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 87 percent / tetrahydrofuran; hexane / 18 h / 20 °C

3.1: 86 percent / pyridinum chlorochromate; Celite / CH₂Cl₂ / 19 h / 20 °C

4.1: 96 percent / aq. p-TsOH / dioxane / 20 h / 55 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Celite; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 1.1: Substitution / 2.1: Metallation / 2.2: Substitution / 3.1: Oxidation / 4.1: Hydrolysis;

DOI:10.1039/b002984j

upstream raw materials:

6-bromo-2-hydroxy-3-methoxybenzaldehyde

sodium methylate

methanol

2,3-dihydro-2,3-dihydroxy-4,7-dimethoxy-2-methylbenzofuran

Downstream raw materials:

2-benzyloxy-3,6-dimethoxybenzaldehyde

C₁₄H₁₆O₆

C₁₃H₁₈O₆

3,6-dimethoxy-4,5-dichlorocatechol

Refernces

• 1、 -. "LIQUID CRYSTAL COMPOUND COMPRISING TWO CONDENSED AND SUBSTITUTED RINGS". Page/Page column 60-61. . Retrieved 2008/06/13.
• 2、 Capecchi, Tanya,De Koning, Charles B.,Michael, Joseph P.. "Nitroalkenes as precursors to the aromatic spiroketal skeleton of γ- rubromycin. A Nef-type reaction mediated by Pearlman's catalyst". . p. 5429 - 5432. Retrieved 2007/10/03.