1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester
• CAS No.: 954416-16-1
• Molecular Formula: C₂₉H₂₈O₇
• Molecular Weight: 488.537
• Mol file: 954416-16-1.mol

Synonyms:1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

Chemical Property of 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

There total 7 articles about 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester 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: 34.0%

tert-butyl 1-bromomethyl-3-methoxy-9,10-anthraquinone-2-carboxylate (954416-13-8) + (3-methoxy-2-tributylstannanylphenyl)methanol (954416-15-0) → 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester (954416-16-1) + tert-butyl 3-methoxy-1-methyl-9,10-anthraquinone-2-carboxylate (954416-11-6)

Guidance literature:

With triphenyl-arsane; copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 75 ℃; for 20h;

DOI:10.1055/s-2007-986652

Reference yield: 17.0%

tert-butyl 1-bromomethyl-3-methoxy-9,10-anthraquinone-2-carboxylate (954416-13-8) + (3-methoxy-2-tributylstannanylphenyl)methanol (954416-15-0) → 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester (954416-16-1)

Guidance literature:

With copper(l) iodide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 80 ℃; for 20h;

Reference yield:

3-hydroxy-1-methyl-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester (954416-09-2) → 1-(2-hydroxymethyl-6-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester (954416-16-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / potassium carbonate / Heating

2: N-bromosuccinimide; benzoyl peroxide

3: triphenyl arsine / Pd₂(dba)3; copper(I) iodide / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 20 h / 75 °C

With N-Bromosuccinimide; triphenyl-arsane; potassium carbonate; dibenzoyl peroxide; copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 3: Stille coupling;

DOI:10.1055/s-2007-986652

upstream raw materials:

tert-butyl 1-bromomethyl-3-methoxy-9,10-anthraquinone-2-carboxylate

(3-methoxy-2-tributylstannanylphenyl)methanol

tert-butyl 3-(trimethylsilyloxy)-2-(1'-(trimethylsilyloxy)vinyl)but-2-enoate

3-hydroxy-1-methyl-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

Downstream raw materials:

tert-butyl 1-(2'-formyl-6'-methoxybenzyl)-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

tert-butyl 1-[2'-(5''-carboxypentanoyl)-6'-methoxybenzyl]-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

1-[2-(1,6-dihydroxyhexyl)-6-methoxybenzyl]-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid tert-butyl ester

C₃₄H₃₄O₈