1-Methyl-2-oxocyclohexanecarboxylic acid

Base Information

• Chemical Name: 1-Methyl-2-oxocyclohexanecarboxylic acid
• CAS No.: 152212-62-9
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.181
• DSSTox Substance ID: DTXSID60462201
• Mol file: 152212-62-9.mol

Synonyms:152212-62-9;1-Methyl-2-oxocyclohexanecarboxylic acid;1-methyl-2-oxocyclohexane-1-carboxylic acid;152212-15-2;Cyclohexanecarboxylic acid, 1-methyl-2-oxo- (9CI);152212-38-9;Cyclohexanecarboxylic acid, 1-methyl-2-oxo-, (+)- (9CI);Cyclohexanecarboxylic acid, 1-methyl-2-oxo-, (-)- (9CI);Cyclohexanecarboxylicacid, 1-methyl-2-oxo-, (-)-;SCHEMBL3170;DTXSID60462201;methylcyclohexanone carboxylic acid;SSNKQVCRNSRBRB-UHFFFAOYSA-N;AKOS026736360

Chemical Property of 1-Methyl-2-oxocyclohexanecarboxylic acid

Chemical Property:

• Boiling Point: 299.1±33.0 °C(Predicted)
• PKA: 3.56±0.20(Predicted)
• PSA: 54.37000
• Density: 1.168±0.06 g/cm3(Predicted)
• LogP: 1.22040
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 198

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCCC1=O)C(=O)O

Technology Process of 1-Methyl-2-oxocyclohexanecarboxylic acid

There total 3 articles about 1-Methyl-2-oxocyclohexanecarboxylic acid 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: 92.0%

ethyl 1-methyl-2-oxocyclohexancarboxylate (66088-37-7,5453-94-1) → 1-methyl-2-oxocyclohexanecarboxylic acid (32116-62-4,152212-38-9,152212-62-9)

Guidance literature:

With water; sodium hydroxide;

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 1-methyl-2-oxocyclohexanecarboxylic acid (32116-62-4,152212-38-9,152212-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium ethanolate; indium (III) iodide / ethanol / 18 h / 20 °C / Cooling with ice

2: water; sodium hydroxide

With indium (III) iodide; water; sodium ethanolate; sodium hydroxide; In ethanol;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 2-n-Butylthiomethylen-cyclohexanon (32116-69-1) → 1-methyl-2-oxocyclohexanecarboxylic acid (32116-62-4,152212-38-9,152212-62-9)

Guidance literature:

Multistep reaction; (i) Li, liq. NH₃, H₂O, Et₂O, (ii) /BRN= 1900390/;

DOI:10.1021/ja00733a042

upstream raw materials:

carbon dioxide

2-n-Butylthiomethylen-cyclohexanon

ethyl 1-methyl-2-oxocyclohexancarboxylate

ethyl 2-oxocyclohexane carboxylate

Downstream raw materials:

racemate trans-2-hydroxy-1-methylcyclohexanecarboxylic acid

(+)-(1S,2R)-2-hydroxy-1-methylcyclohexane carboxylic acid

(2S)-2-methyl-2-(2-propen-1-yl)cyclohexanone

Refernces

• 1、 Muthusamy, Sengodagounder,Babu, Srinivasarao Arulananda,Gunanathan, Chidambaram,Ganguly, Bishwajit,Suresh, Eringathodi,Dastidar, Parthasarathi. "Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks.". . p. 8019 - 8033. Retrieved 2007/10/03.
• 2、 Muthusamy, Sengodagounder,Arulananda Babu, Srinivasarao,Gunanathan, Chidambaram,Suresh, Eringathodi,Dastidar, Parthasarathi,Vir Jasra, Raksh. "Facile synthesis of oxatricyclic systems with various ring sizes and substituents". . p. 6307 - 6318. Retrieved 2007/10/03.