ethyl 4-oxoretinoate

Base Information

• Chemical Name: ethyl 4-oxoretinoate
• CAS No.: 72526-76-2
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.478
• Mol file: 72526-76-2.mol

Synonyms:ethyl 4-oxoretinoate

Chemical Property of ethyl 4-oxoretinoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 4-oxoretinoate

There total 2 articles about ethyl 4-oxoretinoate 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: 60.0%

ethyl (E)-3-formyl-2-butenoate (62054-49-3) + (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0) → ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate (72526-76-2,112924-96-6) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; 1) -20 - -24 deg C, 8 min; 2) room temperature, 2 h;

Reference yield:

canthaxanthin (514-78-3) + ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate → ethyl (11Z)-4-oxoretinoate (112924-96-6) + ethyl 4-oxoretinoate (72526-76-2) + C27H36O3 + C27H36O3 (1332483-29-0)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 20 ℃; for 96h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.06.086

Reference yield: 100.0%

ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate (72526-76-2,112924-96-6) → rac-(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid ethyl ester (81121-21-3,112853-86-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 20h;

upstream raw materials:

ethyl (E)-3-formyl-2-butenoate

(2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

canthaxanthin

Downstream raw materials:

4-ketoretinoic acid

rac-(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid ethyl ester

4-hydroxyretinoic acid