3-[(Benzyloxy)methyl]cyclohexanone

Base Information

• Chemical Name: 3-[(Benzyloxy)methyl]cyclohexanone
• CAS No.: 108743-93-7
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• DSSTox Substance ID: DTXSID40551147
• Mol file: 108743-93-7.mol

Synonyms:3-[(benzyloxy)methyl]cyclohexanone;108743-93-7;3-benzyloxymethylcyclohexanone;SCHEMBL7279180;DTXSID40551147;HQYNKMFMUGOJEZ-UHFFFAOYSA-N;AKOS015906917;3-[(Benzyloxy)methyl]cyclohexan-1-one;3-(phenylmethoxy-methyl)-cyclohexan-1-one

Chemical Property of 3-[(Benzyloxy)methyl]cyclohexanone

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 219

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC(=O)C1)COCC2=CC=CC=C2

Technology Process of 3-[(Benzyloxy)methyl]cyclohexanone

There total 18 articles about 3-[(Benzyloxy)methyl]cyclohexanone 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: 22.0%

cyclohexenone (930-68-7) + C8H9CuO*C8H9LiO → rac-3-butylcyclohexanone (39178-69-3) + 3-<(benzyloxy)methyl>cyclohexan-1-one (108743-93-7)

Guidance literature:

In diethyl ether; at -50 - -45 ℃; for 0.5h;

DOI:10.1021/ja00250a029

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 3-<(benzyloxy)methyl>cyclohexan-1-one (108743-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, 2.) n-BuLi / 1.) THF, DMF, 2.) THF, Et₂O, -78 deg C, 50 min

2: 1.) copper(I)bromide-dimethyl sulfide complex, 2.) n-butyllithium, 3.) boron trifluoride etherate / 1.) isopropylmagnesium chloride / 1.) diisopropyl sulfide, THF, -78 deg C, 20 min, 2.) hexane, -78 deg C, 10 min, 3.) THF, diisopropyl sulfide, hexane, -78 deg C, 15 min, 0 deg C 3 min

With n-butyllithium; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; sodium hydride; isopropylmagnesium chloride;

DOI:10.1021/ja00250a029

Reference yield:

jones reagent (chromic anhydride acid-sulfuric acid) + 3-benzyloxymethylcyclohexanol → 3-<(benzyloxy)methyl>cyclohexan-1-one (108743-93-7)

Guidance literature:

In methanol; acetone;

upstream raw materials:

cyclohexenone

benzyloxymethyl lithium

4-<(benzyloxy)methyl>cyclohexene

3-<(benzyloxy)methyl>cyclohexene

Downstream raw materials:

(1R,3S)-3-Benzyloxymethyl-cyclohexanol

trans-3-<(benzyloxy)methyl>-1-cyclohexanol