(R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin

Base Information

• Chemical Name: (R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin
• CAS No.: 7736-76-7
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.241
• Mol file: 7736-76-7.mol

Synonyms:(R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin

Chemical Property of (R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin

Chemical Property:

• PSA: 35.53000
• LogP: 2.10500

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin

There total 4 articles about (R)-3,4-Dihydro-8-methoxy-3,5-dimethylisocoumarin 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: 60.0%

(R)-N-(tert-butyl)-2-(2-hydroxypropyl)-6-methoxy-3-methylbenzamide → 3,5-dimethyl-8-methoxy-3,4-dihydroisocoumarin (7736-76-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 2h; Reflux;

DOI:10.1016/j.bmc.2019.03.060

Reference yield:

N-(tert-butyl)-2-(2-hydroxypropyl)-6-methoxy-3-methylbenzamide → (3S)-3,4-dihydro-8-methoxy-3,5-dimethyl-1H-2-benzopyran-1-one (7736-76-7,24350-99-0,67549-64-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 2h; Reflux;

DOI:10.1016/j.bmc.2019.03.060

Reference yield:

N-(tert-butyl)-2-methoxy-5-methylbenzamide → 3,5-dimethyl-8-methoxy-3,4-dihydroisocoumarin (7736-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 7 h / -78 °C

2.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/j.bmc.2019.03.060

upstream raw materials:

2-methoxy-5-methylbenzoic acid

Downstream raw materials:

3,4-dihydro-(3R)-5-dimethyl-8-hydroxyisocoumarin

Refernces

• 1、 Huang, Chao,Xiong, Juan,Guan, Hui-Da,Wang, Chang-Hong,Lei, Xinsheng,Hu, Jin-Feng. "Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors". . p. 2027 - 2040. Retrieved 2019/04/10.