2-Methylcyclohex-1-ene-1-carbonyl chloride

Base Information

• Chemical Name: 2-Methylcyclohex-1-ene-1-carbonyl chloride
• CAS No.: 74517-10-5
• Molecular Formula: C8H11 Cl O
• Molecular Weight: 158.62534
• DSSTox Substance ID: DTXSID70597538
• Wikidata: Q82493113
• Mol file: 74517-10-5.mol

Synonyms:74517-10-5;2-Methylcyclohex-1-ene-1-carbonyl chloride;SCHEMBL8041732;DTXSID70597538

Chemical Property of 2-Methylcyclohex-1-ene-1-carbonyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 2.64230
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 158.0498427
• Heavy Atom Count: 10
• Complexity: 182

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CCCC1)C(=O)Cl

Technology Process of 2-Methylcyclohex-1-ene-1-carbonyl chloride

There total 4 articles about 2-Methylcyclohex-1-ene-1-carbonyl chloride 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:

2-methyl-1-cyclohexenecarboxylic acid (13148-94-2) → 2-Methyl-1-cyclohex-1-ene carboxylic acid chloride (74517-10-5)

Guidance literature:

With thionyl chloride; In chloroform; at 0 ℃;

DOI:10.1016/S0957-4166(00)00112-9

Reference yield:

Ethyl 2-methyl-1-cyclohex-1-ene carboxylate (104654-69-5) → 2-Methyl-1-cyclohex-1-ene carboxylic acid chloride (74517-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / aq. KOH / methanol / 4 h / Heating

2: SOCl₂ / CHCl₃ / 0 °C

With potassium hydroxide; thionyl chloride; In methanol; chloroform; 1: Hydrolysis / 2: Substitution;

DOI:10.1002/(SICI)1521-3765(20000317)6:6<949::AID-CHEM949>3.0.CO;2-H

Reference yield:

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 2-Methyl-1-cyclohex-1-ene carboxylic acid chloride (74517-10-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / toluene / 1.5 h / 85 °C

1.2: 2 h / 0 °C

2.1: copper(l) cyanide / diethyl ether / 0.5 h / -50 °C / Inert atmosphere

2.2: 0.5 h / -50 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 20 - 70 °C / Inert atmosphere

4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 20 °C / Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; copper(l) cyanide; sodium hydride; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;

DOI:10.1002/anie.201305218

upstream raw materials:

2-methyl-1-cyclohexenecarboxylic acid

Ethyl 2-methyl-1-cyclohex-1-ene carboxylate

ethyl 2-oxocyclohexane carboxylate

ethyl 2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate

Downstream raw materials:

(E)-naphthalen-2-yl 3-(benzhydryloxy)-2-methyl-4-(2-methylcyclohex-1-en-1-yl)-4-oxobut-2-enoate

(1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate

(E)-phenyl 3-(benzhydryloxy)-2-methyl-4-(2-methylcyclohex-1-en-1-yl)-4-oxobut-2-enoate

Refernces

• 1、 Jolit, Anais,Vazquez-Rodriguez, Saleta,Yap, Glenn P. A.,Tius, Marcus A.. "Diastereospecific nazarov cyclization of fully substituted dienones: Generation of vicinal all-carbon-atom quaternary stereocenters". supporting information. p. 11102 - 11105. Retrieved 2013/10/22.
• 2、 Besson, Michele,Delbecq, Francoise,Gallezot, Pierre,Neto, Samuel,Pinel, Catherine. "Asymmetric synthesis of 2-methyl cyclohexane carboxylic acids by heterogeneous catalysis: Mechanistic aspects". . p. 949 - 958. Retrieved 2007/10/03.