1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Base Information

• Chemical Name: 1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone
• CAS No.: 81325-85-1
• Molecular Formula: C10H11ClO4
• Molecular Weight: 230.648
• DSSTox Substance ID: DTXSID10400072
• Wikidata: Q82202899
• Mol file: 81325-85-1.mol

Synonyms:1-(3-chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone;81325-85-1;Ethanone, 1-(3-chloro-2-hydroxy-4,6-dimethoxyphenyl)-;DTXSID10400072;AKOS022657567

Chemical Property of 1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 230.0345865
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=C(C=C1OC)OC)Cl)O

Technology Process of 1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone

There total 8 articles about 1-(3-Chloro-2-hydroxy-4,6-dimethoxyphenyl)ethanone 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: 94.0%

Acetic acid 2-chloro-3,5-dimethoxy-phenyl ester (131939-10-1) → 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone (81325-85-1)

Guidance literature:

With aluminium trichloride; In chlorobenzene; for 0.5h; Heating;

DOI:10.1021/ja00022a075

Reference yield: 35.0%

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone (81325-85-1)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; for 24h; Reflux; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.08.035

Reference yield:

chloroglucinol dimethyl ether (18113-21-8) → 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone (81325-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pyridine

2: 94 percent / AlCl₃ / chlorobenzene / 0.5 h / Heating

With pyridine; aluminium trichloride; In chlorobenzene;

DOI:10.1021/ja00022a075

upstream raw materials:

chloroglucinol dimethyl ether

acetyl chloride

Acetic acid 2-chloro-3,5-dimethoxy-phenyl ester

3'-amino-2'-hydroxy-4',6'-dimethoxyacetophenone

Downstream raw materials:

1-[3-Chloro-4,6-dimethoxy-2-((E)-(S)-1-methyl-but-2-enyloxy)-phenyl]-ethanone

7-chloro-4,6-dimethoxy-3-methyl-benzofuran-2-carbaldehyde-(2,4-dinitro-phenylhydrazone)

(2-acetyl-6-chloro-3,5-dimethoxy-phenoxy)-acetic acid methyl ester

(2-acetyl-6-chloro-3,5-dimethoxy-phenoxy)-acetic acid

Refernces

• 1、 Pirrung,Brown,Rege,Laughton. "Total synthesis of (+)-griseofulvin". . p. 8561 - 8562. Retrieved 2007/10/02.