trans-3-t-butylcyclohexanecarbonitrile

Base Information

• Chemical Name: trans-3-t-butylcyclohexanecarbonitrile
• CAS No.: 84784-46-3
• Molecular Formula: C₁₁H₁₉N
• Molecular Weight: 165.279
• Mol file: 84784-46-3.mol

Synonyms:

Chemical Property of trans-3-t-butylcyclohexanecarbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-t-butylcyclohexanecarbonitrile

There total 3 articles about trans-3-t-butylcyclohexanecarbonitrile 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%

(+/-)-toluene-4-sulfonic acid-(cis-3-tert-butyl-cyclohexyl ester) (19123-26-3,19123-27-4,31062-01-8,61138-74-7) + sodium cyanide (143-33-9,25596-52-5) → trans-3-t-butylcyclohexanecarbonitrile (84784-46-3)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; at 90 ℃; for 20h;

Reference yield:

hydrogen cyanide (74-90-8) + 4-tert-butylcylohexene (2228-98-0) → trans-4-tert-Butylcyclohexanecarbonitrile (15619-18-8) + 3-(tert-butyl)cyclohexane-1-carbonitrile (84784-46-3)

Guidance literature:

Pd(diop)2;

DOI:10.1016/S0040-4039(00)87174-9

Reference yield:

4-tert-butylcylohexene (2228-98-0) + 1-methylcyclohexa-2,5-diene-1-carbonitrile → trans-4-tert-Butylcyclohexanecarbonitrile (15619-18-8) + 3-(tert-butyl)cyclohexane-1-carbonitrile (84784-46-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(pentafluorophenyl)borate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 110 ℃; for 20h; Overall yield = 91 %; Overall yield = 75 mg; diastereoselective reaction; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.8b10651

upstream raw materials:

hydrogen cyanide

4-tert-butylcylohexene

(+/-)-toluene-4-sulfonic acid-(cis-3-tert-butyl-cyclohexyl ester)

sodium cyanide

Refernces

• 1、 Jackson, Roy W.,Lovel, Craig G.. "THE STEREOCHEMISTRY OF METAL CATALYSED HYDROGEN CYANIDE ADDITION TO ALKENES". . p. 1621 - 1624. Retrieved 2007/10/02.