20,14-retro-Retinoic acid

Base Information

• Chemical Name: 20,14-retro-Retinoic acid
• CAS No.: 138093-35-3
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 138093-35-3.mol

Synonyms:

Chemical Property of 20,14-retro-Retinoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 20,14-retro-Retinoic acid

There total 6 articles about 20,14-retro-Retinoic acid 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:

retinyl palmitate (79-81-2) → 20,14-retro-Retinoic acid (138093-35-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C

2: 58 percent / MnO₂, NaCN / acetonitrile; acetic acid / 62 h / 20 °C

3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating

4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; potassium hydroxide; sodium cyanide; lithium diisopropyl amide; In ethanol; acetic acid; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm00081a020

Reference yield:

retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,22737-97-9,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9) → 20,14-retro-Retinoic acid (138093-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / MnO₂, NaCN / acetonitrile; acetic acid / 62 h / 20 °C

2: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating

3: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; potassium hydroxide; sodium cyanide; lithium diisopropyl amide; In ethanol; acetic acid; acetonitrile;

DOI:10.1021/jm00081a020

Reference yield:

ethyl retinoate (3899-20-5,51249-34-4,59699-82-0,85354-08-1,86708-67-0,86708-68-1,86708-69-2,86708-70-5,24519-09-3) → 20,14-retro-Retinoic acid (138093-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating

2: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium diisopropyl amide; In ethanol;

DOI:10.1021/jm00081a020

upstream raw materials:

2-iodo-propane

all-trans-retinoic-acid

methyl iodide

retinyl palmitate