Ethyl 4-methyl-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl 4-methyl-2-oxocyclohexanecarboxylate
• CAS No.: 13537-82-1
• Molecular Formula: C10H16 O3
• Molecular Weight: 184.235
• Hs Code.: 2918300090
• European Community (EC) Number: 236-910-1
• NSC Number: 84213
• UNII: W2M3GXD5L3
• DSSTox Substance ID: DTXSID60928978
• Nikkaji Number: J241.179B
• Mol file: 13537-82-1.mol

Synonyms:13537-82-1;Ethyl 4-methyl-2-oxocyclohexanecarboxylate;Ethyl 4-methyl-2-cyclohexanone-1-carboxylate;ethyl 4-methyl-2-oxocyclohexane-1-carboxylate;Cyclohexanecarboxylic acid, 4-methyl-2-oxo-, ethyl ester;W2M3GXD5L3;Ethyl-4-methyl-2-cyclohexanone-1-carboxylate;EINECS 236-910-1;NSC-84213;AI3-18159;UNII-W2M3GXD5L3;SCHEMBL127645;DTXSID60928978;NSC84213;CCG-40479;MFCD00001632;NSC 84213;AKOS015913914;SB46036;SB46085;5-methyl-2-(ethoxycarbonyl)cyclohexanone;Ethyl4-methyl-2-oxocyclohexanecarboxylate;2-CARBETHOXY-5-METHYLCYCLOHEXANONE;AS-43459;CS-0204500;Ethyl 4-methyl-2-oxocyclohexanecarboxylate #;FT-0744754;2-ETHOXYCARBONYL-5-METHYLCYCLOHEXANONE;5-METHYL-2-ETHOXYCARBONYLCYCLOHEXANONE;racemic ethyl 4-methyl-2-oxocyclohexanecarboxylate;2-Oxo-4-methylcyclohexanecarboxylic acid ethyl ester;J-006690;Cyclohexanecarboxylicacid,4-methyl-2-oxo-,ethyl ester;4-Methyl-2-cyclohexanone-1-carboxylic acid, ethyl ester;4-METHYL-2-OXOCYCLOHEXANECARBOXYLIC ACID ETHYL ESTER

Chemical Property of Ethyl 4-methyl-2-oxocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.0652mmHg at 25°C
• Melting Point: 53-54 °C
• Refractive Index: n20/D 1.473(lit.)
• Boiling Point: 128-132 °C32 mm Hg(lit.)
• PKA: 12.09±0.40(Predicted)
• Flash Point: >230 °F
• PSA: 43.37000
• Density: 1.045 g/mL at 25 °C(lit.)
• LogP: 1.55480
• Water Solubility.: 2.56g/L at 20℃
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl 4-methyl-2-cyclohexanone-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCC(CC1=O)C
• Uses: Reactant involved in:? ;Hydroxylation / oxidative chlorination with hydrogen peroxide1? ;Heterocyclization2? ;Cyclization of generated dianions followed by dehydrogenation3? ;Palladium-catalyzed isomerization4? ;Regioselective cyclizations5? ;Vinylogous Michael reactions6 2-Carbethoxy-5-methylcyclohexanone is a useful chemical reagent in organic synthesis. It is reported that 2-Carbethoxy-5-methylcyclohexanone is used in the synthesis of optically active α-methylene γ-butyrolactones and (+)-mintlactone. Reactant involved in:Hydroxylation / oxidative chlorination with hydrogen peroxideHeterocyclizationCyclization of generated dianions followed by dehydrogenationPalladium-catalyzed isomerizationRegioselective cyclizationsVinylogous Michael reactions

Technology Process of Ethyl 4-methyl-2-oxocyclohexanecarboxylate

There total 10 articles about Ethyl 4-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:

ethyl 4-methyl-2-oxocyclohex-3-ene-1-carboxylate (14619-42-2) → ethyl 4-methyl-2-cyclohexanone-1-carboxylate (13537-82-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

Reference yield:

oxalic acid diethyl ester (95-92-1) + 3-Methylcyclohexanone (591-24-2,625-96-7) → ethyl 4-methyl-2-cyclohexanone-1-carboxylate (13537-82-1)

Guidance literature:

With sodium ethanolate; at -15 ℃; Erhitzen des Reaktionsprodukts bis auf 220grad;

Reference yield:

→ ethyl 4-methyl-2-cyclohexanone-1-carboxylate (13537-82-1)

Guidance literature:

With palladium on activated charcoal; ethanol; Hydrogenation;

upstream raw materials:

ethanol

4-methyl-2-oxo-cyclohexanecarboxylic acid

oxalic acid diethyl ester

3-Methylcyclohexanone

Downstream raw materials:

1-allyl-4-methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester

4-methyl-1-[2]naphthylmethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester

9-methyl-3-hydroxy-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one

(+/-)-1-hydroxy-9-methyl-3-pentyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one

Refernces

• 1、 Pollini,Barco,Patri,De Giuli. "The cyclization of 2-p-tosyloxymethylene-2-benzyloxymethylene-5-methyl-1-cyclohexanone". . p. 850 - 860. Retrieved 2007/10/08.