(3R,4R)-ω-carboxy-o-cannabidiol

Base Information

• Chemical Name: (3R,4R)-ω-carboxy-o-cannabidiol
• CAS No.: 120467-25-6
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• Mol file: 120467-25-6.mol

Synonyms:

Chemical Property of (3R,4R)-ω-carboxy-o-cannabidiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-ω-carboxy-o-cannabidiol

There total 6 articles about (3R,4R)-ω-carboxy-o-cannabidiol 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: 22.0%

(1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6) + 5-(3,5-dihydroxyphenyl)pentanoic acid (74356-41-5) → (3R,4R)-ω-carboxy-p-cannabidiol (63998-82-3) + (3R,4R)-ω-carboxy-o-cannabidiol (120467-25-6) + 5-[3,5-Dihydroxy-2,4-bis-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-pentanoic acid (120467-26-7)

Guidance literature:

With toluene-4-sulfonic acid; In diethyl ether; benzene; 1.) 25 deg C, 30 min, 2.) 50 deg C, 5 min;

Reference yield: 13.6%

(1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6) + 5-(3,5-dihydroxyphenyl)pentanoic acid (74356-41-5) → (3R,4R)-ω-carboxy-p-cannabidiol (63998-82-3) + (3R,4R)-ω-carboxy-o-cannabidiol (120467-25-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; at 18 - 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00009

Reference yield:

5-(3,5-dimethoxyphenyl)pentanoic acid ethyl ester (197178-54-4) → (3R,4R)-ω-carboxy-p-cannabidiol (63998-82-3) + (3R,4R)-ω-carboxy-o-cannabidiol (120467-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide / acetic acid / Reflux; Inert atmosphere

2: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 0.5 h / 18 - 25 °C / Inert atmosphere

With hydrogen bromide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/acsmedchemlett.6b00009

upstream raw materials:

(1S,4R)-p-mentha-2,8-dien-1-ol

5-(3,5-dihydroxyphenyl)pentanoic acid

5-(3',5'-dimethoxyphenyl)-2-(methoxycarbonyl)penta-2(E),4(E)-dienoic acid

3,5-dimethoxybenzaldehdye

Refernces

• 1、 Crombie, Leslie,Crombie, W. Mary L.,Tuchinda, Patoomratana. "Synthesis of Cannabinoids Carrying ω-Carboxy Substituents: The Cannabidiols, Cannabinol and Δ1- and Δ6-Tetrahydrocannabinols of this Series". . p. 1255 - 1262. Retrieved 2007/10/02.