methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate
• CAS No.: 22249-33-8
• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.316
• Mol file: 22249-33-8.mol

Synonyms:

Chemical Property of methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate

There total 7 articles about methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate 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: 79.0%

2-bromomethyl-2-methoxycarbonyl-4-tert-butylcyclohexanone → 2-Carbomethoxy-2-methyl-4-t-butylcyclohexanon (22249-33-8,87373-04-4) + 3-tert-butyl-6-oxo-cycloheptanecarboxylic acid methyl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 13h; Heating;

DOI:10.1016/S0040-4020(98)00467-0

Reference yield: 79.0%

2-bromomethyl-2-methoxycarbonyl-4-tert-butylcyclohexanone → 2-Carbomethoxy-2-methyl-4-t-butylcyclohexanon (22249-33-8,87373-04-4) + 3-tert-butyl-6-oxo-cycloheptanecarboxylic acid methyl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 13h; Heating;

DOI:10.1016/S0040-4020(98)00467-0

Reference yield:

4-tercbutyl-cyclohexanone (98-53-3) → methyl trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylate (22249-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diisopropylamine, 1,10-phenanthroline, n-BuLi / 1.) ether, 1 deg C, 1 h, 2.) 1 deg C, 35 min, 1 deg C to room temp. 30 min

2: 40percent aq. KOH / diethyl ether / 0 °C

3: 8.5 g / CH₃ONa / methanol; xylene / 1.) 3 h, 45 deg C, 2.) 12 h, room temp., 3.) 1 h, reflux

With potassium hydroxide; n-butyllithium; 1,10-Phenanthroline; sodium methylate; diisopropylamine; In methanol; diethyl ether; xylene;

DOI:10.1021/jo00172a011

upstream raw materials:

5-tert-butyl-2-oxocyclohexanecarboxylic acid methyl ester

methyl iodide

4-tercbutyl-cyclohexanone

Downstream raw materials:

trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylic acid

(1S,2S,4R)-4-tert-Butyl-2-hydroxymethyl-2-methyl-cyclohexanol

(1SR,2RS,4SR)-4-(tert-butyl)-2-(hydroxymethyl)-2-methylcyclohexan-1-ol

Refernces

• 1、 Kayser, Robert H.,Brault, Margaret,Pollack, Ralph M.,Bantia, Shanta,Sadoff, Scott F.. "Kinetics of Decarboxylation of the Two Epimers of 5-tert-Butyl-1-methyl-2-oxocyclohexanecarboxylic Acid: Lack of Stereoelectronic Control in β-Keto Acid Decarboxylation". . p. 4497 - 4502. Retrieved 2007/10/02.