Hexanal, 6-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-

Base Information

• Chemical Name: Hexanal, 6-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-
• CAS No.: 144180-82-5
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• Mol file: 144180-82-5.mol

Synonyms:

Chemical Property of Hexanal, 6-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexanal, 6-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)-

There total 6 articles about Hexanal, 6-(3,5-dimethyl-4-oxo-2,5-cyclohexadien-1-ylidene)- 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:

6-(3,5-dimethyl-4-hydroxyphenyl)hexanal (144180-79-0) → 6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal (144180-82-5)

Guidance literature:

With silver(l) oxide; In benzene-d6; at 65 ℃; for 2h;

DOI:10.1021/jo00051a038

Reference yield:

hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) → 6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal (144180-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) t-BuLi / 1.) pentane, ether, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

2: 99 percent / H₂ / 5percent Pd/C / ethanol / 12 h / 760 Torr

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 1 h

4: 121 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

5: Ag₂O / benzene-d6 / 2 h / 65 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; benzene-d6;

DOI:10.1021/jo00051a038

Reference yield:

1-Bromo-4<(tert-butyldimethylsilyl)oxy>-3,5-dimethylbenzene (139229-99-5) → 6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal (144180-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) t-BuLi / 1.) pentane, ether, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

2: 99 percent / H₂ / 5percent Pd/C / ethanol / 12 h / 760 Torr

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 1 h

4: 121 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

5: Ag₂O / benzene-d6 / 2 h / 65 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; benzene-d6;

DOI:10.1021/jo00051a038

upstream raw materials:

6-(3,5-dimethyl-4-hydroxyphenyl)hexanal

hexahydro-2H-oxepin-2-one

1-Bromo-4<(tert-butyldimethylsilyl)oxy>-3,5-dimethylbenzene

6-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>hexanol

Downstream raw materials:

(1S*,2S*)- and (1R*,2S*)-2-(3,5-dimethyl-4-hydroxyphenyl)cyclohexanol