All-E-12,14-ethano-20-norretinal

Base Information

• Chemical Name: All-E-12,14-ethano-20-norretinal
• CAS No.: 155503-54-1
• Molecular Formula: C₂₁H₂₈O
• Molecular Weight: 296.453
• Mol file: 155503-54-1.mol

Synonyms:

Chemical Property of All-E-12,14-ethano-20-norretinal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of All-E-12,14-ethano-20-norretinal

There total 4 articles about All-E-12,14-ethano-20-norretinal 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:

hexanedinitrile (111-69-3) → All-E-12,14-ethano-20-norretinal (155503-54-1)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA / tetrahydrofuran; hexane / 1.) -80 deg C, 30 min; -80 to -45 deg C, 1.5 h, 2.) HMPA, -45 deg C, 10 min

2: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / Ambient temperature

3: Dibal / petroleum ether; hexane / 1.) -70 deg C, 1 h, 2.) -20 deg C

4: aq. acetic acid, SiO₂ / petroleum ether; diethyl ether / 72 h

With silica gel; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; Petroleum ether;

DOI:10.1002/recl.19941130107

Reference yield:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal (3917-41-7) → All-E-12,14-ethano-20-norretinal (155503-54-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / Ambient temperature

2: Dibal / petroleum ether; hexane / 1.) -70 deg C, 1 h, 2.) -20 deg C

3: aq. acetic acid, SiO₂ / petroleum ether; diethyl ether / 72 h

With silica gel; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; Petroleum ether;

DOI:10.1002/recl.19941130107

Reference yield:

C10H16LiN2O3P → All-E-12,14-ethano-20-norretinal (155503-54-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / Ambient temperature

2: Dibal / petroleum ether; hexane / 1.) -70 deg C, 1 h, 2.) -20 deg C

3: aq. acetic acid, SiO₂ / petroleum ether; diethyl ether / 72 h

With silica gel; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; Petroleum ether;

DOI:10.1002/recl.19941130107

upstream raw materials:

hexanedinitrile

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

2-<3-Methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadienylidene>hexanedinitrile