(4-Oxocyclohexyl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (4-Oxocyclohexyl)methyl 4-methylbenzenesulfonate
• CAS No.: 17159-83-0
• Molecular Formula: C14H18 O4 S
• Molecular Weight: 282.3553
• NSC Number: 147468
• DSSTox Substance ID: DTXSID60301929
• Nikkaji Number: J2.752.598I
• Wikidata: Q82046308
• Mol file: 17159-83-0.mol

Synonyms:(4-oxocyclohexyl)methyl 4-methylbenzenesulfonate;17159-83-0;NSC147468;4-(Tosyloxymethyl)cyclohexanone;SCHEMBL3649233;DTXSID60301929;MFCD00795472;NSC 147468;NSC-147468;CS-0093873;(4-oxocyclohexyl)methyl4-methylbenzenesulfonate;D75478

Chemical Property of (4-Oxocyclohexyl)methyl 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 4.91E-08mmHg at 25°C
• Boiling Point: 442.7°C at 760 mmHg
• Flash Point: 221.6°C
• Density: 1.212g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 282.09258022
• Heavy Atom Count: 19
• Complexity: 392

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CCC(=O)CC2

Technology Process of (4-Oxocyclohexyl)methyl 4-methylbenzenesulfonate

There total 4 articles about (4-Oxocyclohexyl)methyl 4-methylbenzenesulfonate 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: 92.6%

4-hydroxymethyl-cyclohexanone (38580-68-6) + p-toluenesulfonyl chloride (98-59-9) → 4-<<(p-tolylsulfonyl)oxy>methyl>cyclohexanone (17159-83-0)

Guidance literature:

With pyridine; at 0 ℃; for 48h;

DOI:10.1021/jo00204a022

Reference yield:

1,4-dioxaspiro[4.5]decan-8-ylmethyl 4-methylbenzenesulfonate (26934-56-5) → 4-<<(p-tolylsulfonyl)oxy>methyl>cyclohexanone (17159-83-0)

Guidance literature:

With sulfuric acid;

Reference yield:

1-<(trimethylsilyl)oxy>cyclohexene-4-carboxaldehyde (94458-92-1) → 4-<<(p-tolylsulfonyl)oxy>methyl>cyclohexanone (17159-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄ / diethyl ether / 1.) from -78 deg C to RT, 2 h, 2.) RT, 30 min

2: 15percent aq. NaOH / methanol / 0.5 h / Ambient temperature

3: 92.6 percent / pyridine / 48 h / 0 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; In methanol; diethyl ether;

DOI:10.1021/jo00204a022

upstream raw materials:

1,4-dioxaspiro[4.5]decan-8-ylmethyl 4-methylbenzenesulfonate

4-hydroxymethyl-cyclohexanone

p-toluenesulfonyl chloride

1-<(trimethylsilyl)oxy>cyclohexene-4-carboxaldehyde

Downstream raw materials:

4-((4-fluorophenoxy)methyl)cyclohexanone

Refernces

• 1、 Radchenko, Dmytro S.,Kopylova, Nataliya,Grygorenko, Oleksandr O.,Komarov, Igor V.. "Conformationally restricted nonchiral pipecolic acid analogues". scheme or table. p. 5541 - 5544. Retrieved 2009/12/04.
• 2、 Nicolaou,Magolda,Claremon. "Carbocyclic thromboxane A2". . p. 1404 - 1409. Retrieved 2007/10/02.