Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate
• CAS No.: 50388-51-7
• Molecular Formula: C10H16O3
• Molecular Weight: 184.235
• Hs Code.: 2918300090
• European Community (EC) Number: 967-049-6
• DSSTox Substance ID: DTXSID20498400
• Mol file: 50388-51-7.mol

Synonyms:50388-51-7;Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate;Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate;Cyclohexanecarboxylic acid, 5,5-dimethyl-2-oxo-, methyl ester;MFCD09869052;methyl5,5-dimethyl-2-oxocyclohexanecarboxylate;SCHEMBL855428;DTXSID20498400;SFXQJROVECIHKO-UHFFFAOYSA-N;AKOS017516446;DS-9782;SY028946;CS-0146427;EN300-243310;A850151

Chemical Property of Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate

Chemical Property:

• PSA: 43.37000
• LogP: 1.55480
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

97% ^*data from raw suppliers

Methyl 5,5-dimethyl-2-oxocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(=O)C(C1)C(=O)OC)C

Technology Process of Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate

There total 2 articles about Methyl 5,5-Dimethyl-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: 95.0%

4,4-dimethylcyclohexane-1-one (4255-62-3) + carbonic acid dimethyl ester (616-38-6) → methyl 5,5-dimethyl-2-oxo-cyclohexanecarboxylate (50388-51-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/jo971935+

Reference yield:

4,4-dimethylcyclohexenone (1073-13-8) → methyl 5,5-dimethyl-2-oxo-cyclohexanecarboxylate (50388-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / H₂ / Pd/C / ethyl acetate / 759.8 Torr

2: 85 percent / NaH, KH / tetrahydrofuran

With hydrogen; potassium hydride; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1139/v97-090

Reference yield: 97.0%

methyl 5,5-dimethyl-2-oxo-cyclohexanecarboxylate (50388-51-7) → 1-Chloro-5,5-dimethyl-2-oxo-cyclohexanecarboxylic acid methyl ester (193144-62-6)

Guidance literature:

With chlorine; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1139/v97-090

upstream raw materials:

4,4-dimethylcyclohexane-1-one

carbonic acid dimethyl ester

4,4-dimethylcyclohexenone

Downstream raw materials:

1-Chloro-5,5-dimethyl-2-oxo-cyclohexanecarboxylic acid methyl ester

6-bromo-4,4-dimethyl-2-carbomethoxycyclohexanone

(1R,2S,6R)-2-({[(R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-butyl]-methyl-amino}-methyl)-6-hydroxymethyl-4,4-dimethyl-cyclohexanol

(1R,2R,6S)-2-(3-Benzyloxy-propoxymethoxymethyl)-6-({[(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-butyl]-methyl-amino}-methyl)-4,4-dimethyl-cyclohexanol