2,3-Dimethoxy-4-methylbenzaldehyde

Base Information

• Chemical Name: 2,3-Dimethoxy-4-methylbenzaldehyde
• CAS No.: 75889-47-3
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• DSSTox Substance ID: DTXSID80435598
• Nikkaji Number: J2.504.739G
• Wikidata: Q82250643
• Mol file: 75889-47-3.mol

Synonyms:2,3-Dimethoxy-4-methylbenzaldehyde;75889-47-3;Benzaldehyde, 2,3-dimethoxy-4-methyl-;SCHEMBL669820;DTXSID80435598;QBIKTQKJHRUMDE-UHFFFAOYSA-N;FT-0710375;EN300-8199075

Chemical Property of 2,3-Dimethoxy-4-methylbenzaldehyde

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2,3-Dimethoxy-4-methylbenzaldehyde

There total 7 articles about 2,3-Dimethoxy-4-methylbenzaldehyde 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: 93.0%

1,2-dimethoxy-3-methylbenzene (4463-33-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,3-dimethoxy-4-methylbenzaldehyde (75889-47-3)

Guidance literature:

1,2-dimethoxy-3-methylbenzene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at 0 - 20 ℃; for 16h; Inert atmosphere;

N,N-dimethyl-formamide; In diethyl ether; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.202101863

Reference yield: 52.0%

1,2-dimethoxy-3-methylbenzene (4463-33-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (2,3-dimethoxyphenyl)acetaldehyde (5707-56-2) + 2,3-dimethoxy-4-methylbenzaldehyde (75889-47-3)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; 1.) 0 deg C, 30 min; r.t., overnight, 2.) 0 deg C, 1 h;

DOI:10.1039/P19960002497

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 2,3-dimethoxy-4-methylbenzaldehyde (75889-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 3.5 h / 20 °C

1.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: TMEDA; t-BuLi / diethyl ether; pentane / 13 h / 20 °C

2.2: 75 percent / diethyl ether; pentane / 0.5 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; hexane; pentane;

DOI:10.1021/ol071228v

upstream raw materials:

1,2-dimethoxy-3-methylbenzene

N,N-dimethyl-formamide

2,3-dimethyoxybenzaldehyde

methyl iodide

Downstream raw materials:

2,3-dimethoxy-1-methyl-4-vinylbenzene

(2E,5E)-2,5-bis(2,3-dimethoxy-4-methylbenzylidene)cyclopentanone

2,3-dihydroxy-4-methyl-benzaldehyde

(S)-4-(2,3-dimethoxy-4-methylphenyl)pentanenitrile