rac-neomenthyl-4-tolylsulfonate

Base Information

• Chemical Name: rac-neomenthyl-4-tolylsulfonate
• CAS No.: 14539-76-5
• Molecular Formula: C₁₇H₂₆O₃S
• Molecular Weight: 310.458
• Mol file: 14539-76-5.mol

Synonyms:rac-neomenthyl-4-tolylsulfonate

Chemical Property of rac-neomenthyl-4-tolylsulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-neomenthyl-4-tolylsulfonate

There total 5 articles about rac-neomenthyl-4-tolylsulfonate 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%

menthol (89-78-1) + toluene-4-sulfonic acid (104-15-4) → (-)-menthyl tosylate (2230-77-5,2230-82-2,2230-91-3,7212-65-9,14539-75-4,14539-76-5,60183-51-9,63559-37-5)

Guidance literature:

With tetrachlorosilane; In dichloromethane; for 2h; Heating;

DOI:10.1016/j.tetlet.2004.07.076

Reference yield: 81.0%

Neomenthol (2216-52-6) + p-toluenesulfonyl chloride (98-59-9) → (1S,2S,5R)-(+)-2-isopropyl-5-methylcyclohexyl tosylate (2230-82-2,2230-91-3,7212-65-9,14539-75-4,14539-76-5,60183-51-9,63559-37-5,2230-77-5)

Guidance literature:

With pyridine; for 21h; Ambient temperature;

DOI:10.1002/prac.199533701115

Reference yield:

(1S,2R,5S)-(+)-menthol (15356-60-2) → Toluene-4-sulfonic acid (1R,2R)-2-isopropyl-5-methyl-cyclohexyl ester (2230-77-5,2230-82-2,2230-91-3,7212-65-9,14539-75-4,14539-76-5,60183-51-9,63559-37-5)

Guidance literature:

With diethylazodicarboxylate - triphenylphosphine (DEAD-Ph₃P); In benzene; for 48h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)85628-2

upstream raw materials:

menthol

toluene-4-sulfonic acid

Neomenthol

p-toluenesulfonyl chloride

Downstream raw materials:

(1R)-menth-3-ene

4-chloro-p-menthane

8-chloro-p-menthane

Neomenthyl thioacetate

Refernces

• 1、 Demakova,Sudarikov,Rubtsova,Frolova,Kuchin. "Synthesis of new monoterpene sulfonylimidazoles". scheme or table. p. 38 - 42. Retrieved 2012/07/28.
• 2、 Braddock, D. Christopher,Pouwer, Rebecca H.,Burton, Jonathan W.,Broadwith, Phillip. "Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups". supporting information; experimental part. p. 6042 - 6049. Retrieved 2009/12/24.