(+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone

Base Information

• Chemical Name: (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone
• CAS No.: 81509-20-8
• Molecular Formula: C₁₅H₁₅IO₃
• Molecular Weight: 370.187
• Mol file: 81509-20-8.mol

Synonyms:(+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone

Chemical Property of (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone

There total 5 articles about (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone 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:

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone (81509-20-8)

Guidance literature:

With toluene; Behandeln des Reaktionsprodukts in Methanol mit wss. Natriumhydrogencarbonat-Loesung und einer wss. Loesung von Jod und Kaliumjodid;

DOI:10.1021/ja01623a058

Reference yield:

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → (1R,3R,6R,7S,9S)-2-Iodo-9-(4-methoxy-phenyl)-4-oxa-tricyclo[4.2.1.03,7]nonan-5-one (81509-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / dioxane / 60 h / Irradiation

2: 2.) I₂ / 1.) toluene, reflux, 27 d.

With iodine; In 1,4-dioxane;

DOI:10.1016/S0040-4020(01)98883-0

Reference yield:

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5,42996-84-9) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (+/-)-3endo-(4-methoxy-phenyl)-norborn-5-ene-2exo-carboxylic acid (59259-39-1,59286-04-3,59286-08-7,81570-32-3) + (+/-)-6endo-hydroxy-5exo-iodo-3exo-(4-methoxy-phenyl)-norbornane-2endo-carboxylic acid-lactone (81509-20-8)

Guidance literature:

With iodine; sodium hydrogencarbonate; potassium iodide; Multistep reaction; 1.) reflux, 18 h, 2.) 20 min;

DOI:10.1021/jm980566m

upstream raw materials:

(E)-3-(4-methoxyphenyl)acrylic acid

cyclopenta-1,3-diene

(E)-3-(4-methoxyphenyl)propenoyl chloride

(Z)-3-(4-methoxyphenyl)acrylic acid

Downstream raw materials:

acide p-methoxy phenyl-3 endo bicyclo<2.2.1>heptene-5 carboxylique-2 endo

(+/-)-3exo-(4-methoxy-phenyl)-norborn-5-ene-2endo-carboxylic acid

Refernces

• 1、 Nicolas,Beugelmans-Verrier,Guilhem. "-". . p. 3847 - 3860. Retrieved 2007/10/02.