methyl 9Z,11E,13Z-12-methoxycarbonylretinoate

Base Information

• Chemical Name: methyl 9Z,11E,13Z-12-methoxycarbonylretinoate
• CAS No.: 80040-38-6
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.505
• Mol file: 80040-38-6.mol

Synonyms:

Chemical Property of methyl 9Z,11E,13Z-12-methoxycarbonylretinoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 9Z,11E,13Z-12-methoxycarbonylretinoate

There total 3 articles about methyl 9Z,11E,13Z-12-methoxycarbonylretinoate 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:

9-hydroxy-β-ionylideneacetaldehyde dimethyl acetal (1224-76-6) → methyl 9Z,11E,13Z-12-methoxycarbonylretinoate (79985-66-3,80009-88-7,80009-89-8,80040-38-6,99394-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / acetone / 1.5 h / Heating

2: 1) KOH / 1) MeOH, 20 deg C, 64 h; 2) Et₂O, 20 deg C, 6 h

With hydrogenchloride; potassium hydroxide; In acetone;

Reference yield:

methanol (67-56-1) + 13-cis-12-carboxyretinoic anhydride (83860-26-8) → 11-cis-12-carboxyretinoic acid dimethyl ester (80009-88-7) + 13-cis-12-carboxyretinoic acid dimethyl ester (80040-38-6) + all-trans-12-carboxyretinoic acid dimethyl ester (79985-66-3)

Guidance literature:

With hydrogenchloride; iodine; Yield given. Multistep reaction. Yields of byproduct given; 1.) low temperature, 10 d, 2.) Et₂O, hexane, 0 deg C, 12 d;

DOI:10.1021/jo00349a001

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + diethyl 3-methylpent-2-enedioate (924-59-4) + (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal (54226-17-4) → 11-cis,13-cis-12-carboxyretinoic acid dimethyl ester (80009-89-8) + methyl 9Z,11E,13Z-12-methoxycarbonylretinoate (79985-66-3,80009-88-7,80009-89-8,80040-38-6,99394-39-5)

Guidance literature:

With potassium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1) MeOH, 20 deg C, 64 h; 2) Et₂O, 20 deg C, 6 h;

upstream raw materials:

methanol

13-cis-12-carboxyretinoic anhydride

diazomethane

diethyl 3-methylpent-2-enedioate

Downstream raw materials:

11-cis,13-cis-12-carboxyretinoic acid

all-trans-12-carboxyretinoic acid

13-cis-12-carboxyretinoic acid

11-cis,13-cis-12-(Hydroxymethyl)retinol