1-(o-Tolyl)cyclohexan-1-ol

Base Information

• Chemical Name: 1-(o-Tolyl)cyclohexan-1-ol
• CAS No.: 6957-09-1
• Molecular Formula: C13H18O
• Molecular Weight: 190.285
• Hs Code.: 2902909090
• European Community (EC) Number: 230-142-0
• NSC Number: 66196
• DSSTox Substance ID: DTXSID70219824
• Nikkaji Number: J265.998K
• Wikidata: Q83096840
• Mol file: 6957-09-1.mol

Synonyms:1-(2-methylphenyl)cyclohexanol;1-(2-methylphenyl)cyclohexan-1-ol;6957-09-1;1-(o-Tolyl)cyclohexan-1-ol;NSC66196;1-(o-Tolyl)cyclohexanol;SCHEMBL5349864;DTXSID70219824;Cyclohexanol, 1-(2-methylphenyl)-;EINECS 230-142-0;NSC 66196;NSC-66196;AKOS010010599;CS-0246219;EN300-319856;6658-78-2

Chemical Property of 1-(o-Tolyl)cyclohexan-1-ol

Chemical Property:

• Vapor Pressure: 0.000249mmHg at 25°C
• Boiling Point: 311°C at 760 mmHg
• Flash Point: 121.4°C
• PSA: 20.23000
• Density: 1.043g/cm³
• LogP: 3.14670
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 190.135765193
• Heavy Atom Count: 14
• Complexity: 182

Purity/Quality:

99% ^*data from raw suppliers

1-(O-TOLYL)CYCLOHEXANOL AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2(CCCCC2)O

Technology Process of 1-(o-Tolyl)cyclohexan-1-ol

There total 5 articles about 1-(o-Tolyl)cyclohexan-1-ol 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: 87.0%

2-methylphenyl bromide (95-46-5) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-(2-methylphenyl)-1-cyclohexanol (6957-09-1)

Guidance literature:

2-methylphenyl bromide; With n-butyllithium; In diethyl ether; at -78 ℃; Inert atmosphere;

cyclohexanone; In diethyl ether; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja4100595

Reference yield: 63.0%

2-Chlorobenzyl alcohol (17849-38-6) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1-(2-methylphenyl)-1-cyclohexanol (6957-09-1)

Guidance literature:

2-Chlorobenzyl alcohol; With n-butyllithium; 4,4'-di-tert-butylbiphenyl; lithium; In tetrahydrofuran; at -78 ℃; for 0.75h;

cyclohexanone; In tetrahydrofuran; at -78 - 25 ℃;

With benzaldehyde; In tetrahydrofuran; at -40 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00428-9

Reference yield: 44.0%

cyclohexanol (108-93-0) + 5,5-dimethyl-2-(o-tolyl)-1,3,2-dioxaborinane (91994-11-5) → 1-(2-methylphenyl)-1-cyclohexanol (6957-09-1)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium tert-butylate; chlorobenzene; cesium fluoride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 80 ℃; for 9h; Inert atmosphere;

DOI:10.1039/c1cc10826c

upstream raw materials:

ortho-tolylmagnesium bromide

cyclohexanone

2-methylphenyl bromide

2-Chlorobenzyl alcohol

Downstream raw materials:

2-(2-methylphenyl)cyclohex-2-enone

(+/-)-(3-oxo-2t-o-tolyl-cyclohex-t-yl)-acetic acid

1-cyclohexyl-2-methylbenzene

1-(2-methylphenyl)cyclohexylamine

Refernces

• 1、 Wen, Yunming,Chen, Guifang,Huang, Shiqiang,Tang, Yu,Yang, Jun,Zhang, Yuanming. "The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides". . p. 947 - 957. Retrieved 2016/04/05.
• 2、 Rono, Lydia J.,Yayla, Hatice G.,Wang, David Y.,Armstrong, Michael F.,Knowles, Robert R.. "Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization". supporting information. p. 17735 - 17738. Retrieved 2014/01/06.