14-Ethylretinoic acid

Base Information

• Chemical Name: 14-Ethylretinoic acid
• CAS No.: 138093-41-1
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.495
• Mol file: 138093-41-1.mol

Synonyms:

Chemical Property of 14-Ethylretinoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-Ethylretinoic acid

There total 6 articles about 14-Ethylretinoic 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) → 14-Ethylretinoic acid (138093-41-1)

Guidance literature:

Multi-step reaction with 6 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

5: 77 percent / diethyl ether / 20 h / 0 °C

6: 1.) MeONa, 2.) 10percent aq. KOH / 1.) MeOH, reflux, 7 h, 2.) EtOH, reflux

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

DOI:10.1021/jm00081a020

Reference yield:

all-trans-retinoic-acid (302-79-4) → 14-Ethylretinoic acid (138093-41-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 77 percent / diethyl ether / 20 h / 0 °C

3: 1.) MeONa, 2.) 10percent aq. KOH / 1.) MeOH, reflux, 7 h, 2.) EtOH, reflux

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium methylate; lithium diisopropyl amide; In diethyl ether;

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) → 14-Ethylretinoic acid (138093-41-1)

Guidance literature:

Multi-step reaction with 4 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

3: 77 percent / diethyl ether / 20 h / 0 °C

4: 1.) MeONa, 2.) 10percent aq. KOH / 1.) MeOH, reflux, 7 h, 2.) EtOH, reflux

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium methylate; lithium diisopropyl amide; In diethyl ether; ethanol;

DOI:10.1021/jm00081a020

upstream raw materials:

methyl 14-ethyl-20,14-retro-retinoate

retinyl palmitate

all-trans-retinoic-acid

ethyl retinoate

Refernces