3-[6-(3-Formylphenoxy)hexoxy]benzaldehyde

Base Information

• Chemical Name: 3-[6-(3-Formylphenoxy)hexoxy]benzaldehyde
• CAS No.: 112116-24-2
• Molecular Formula: C20H22 O4
• Molecular Weight: 326.392
• DSSTox Substance ID: DTXSID50572661
• Nikkaji Number: J2.599.031E
• Wikidata: Q82461084
• Mol file: 112116-24-2.mol

Synonyms:112116-24-2;3-[6-(3-formylphenoxy)hexoxy]benzaldehyde;3,3'-(1,6-HEXANEDIYLDIOXY)BISBENZALDEHYDE;3,3'-(Hexane-1,6-diylbis(oxy))dibenzaldehyde;3,3'-[Hexane-1,6-diylbis(oxy)]dibenzaldehyde;SCHEMBL8716037;DTXSID50572661;A802489

Chemical Property of 3-[6-(3-Formylphenoxy)hexoxy]benzaldehyde

Chemical Property:

• Boiling Point: 513.1±35.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.134±0.06 g/cm3(Predicted)
• LogP: 4.32980
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 326.15180918
• Heavy Atom Count: 24
• Complexity: 324

Purity/Quality:

99%min ^*data from raw suppliers

3,3'-(1,6-HEXANEDIYLDIOXY)BIS-BENZALDEHYDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)OCCCCCCOC2=CC=CC(=C2)C=O)C=O

Technology Process of 3-[6-(3-Formylphenoxy)hexoxy]benzaldehyde

There total 5 articles about 3-[6-(3-Formylphenoxy)hexoxy]benzaldehyde 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: 82.0%

1 ,6-dibromohexane (629-03-8) + meta-hydroxybenzaldehyde (100-83-4) → 3,3'-[hexane-1,6-diylbis(oxy)]dibenzaldehyde (112116-24-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jacs.6b00538

Reference yield:

1,6-bis(p-toluenesulfonyloxy)hexane (4672-50-8) + meta-hydroxybenzaldehyde (100-83-4) → 3,3'-[hexane-1,6-diylbis(oxy)]dibenzaldehyde (112116-24-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; paraffin; at 80 ℃; for 9h; Yield given; 1.) room temp. 10 min;

DOI:10.1002/(sici)1099-0690(199801)1998:1<149::aid-ejoc149>3.0.co;2-2

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 3,3'-[hexane-1,6-diylbis(oxy)]dibenzaldehyde (112116-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine

2: 1.) NaH / dimethylformamide; tetrahydrofuran; paraffin / 9 h / 80 °C / 1.) room temp. 10 min

With pyridine; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; paraffin;

DOI:10.1002/(sici)1099-0690(199801)1998:1<149::aid-ejoc149>3.0.co;2-2

upstream raw materials:

1 ,6-dibromohexane

meta-hydroxybenzaldehyde

1,6-bis(p-toluenesulfonyloxy)hexane

p-toluenesulfonyl chloride

Downstream raw materials:

(CH₂)6(OC₆H₄CH(OH)CCH)2

2,2'-(3,3'-(hexane-1,6-diylbis(oxy))bis(3,1-phenylene))bis(methan-1-yl-1-ylidene)bis(hydrazinecarbothioamide)

N,N'-(5,5'-(3,3'-(hexane-1,6-diylbis(oxy))bis(3,1-phenylene))bis(4-acetyl-4,5-dihydro-1,3,4-thiadiazole-5,2-diyl))diacetamide

(CH₂)6(OC₆H₄C(O)CCH)2

Refernces

• 1、 Mitra, Nirmal K.,Meudom, Rolande,Corzo, Hector H.,Gorden, John D.,Merner, Bradley L.. "Overcoming Strain-Induced Rearrangement Reactions: A Mild Dehydrative Aromatization Protocol for Synthesis of Highly Distorted p-Phenylenes". supporting information. p. 3235 - 3240. Retrieved 2016/03/19.
• 2、 Saeed, Aamer,Qasim, Muhammad,Hussain, Majid. "Novel Bis(2-(5-((5-phenyl-1H-tetrazol-1-yl)methyl)-4H-1,2,4-triazol-3-yl)phenoxy)Alkanes: Synthesis and Characterization". . p. 1114 - 1118. Retrieved 2015/08/06.