Dimethyl 3-hydroxy-5-methoxyphthalate

Base Information

• Chemical Name: Dimethyl 3-hydroxy-5-methoxyphthalate
• CAS No.: 24953-74-0
• Molecular Formula: C11H12O6
• Molecular Weight: 240.213
• DSSTox Substance ID: DTXSID30564807
• Wikidata: Q82449637
• Mol file: 24953-74-0.mol

Synonyms:Dimethyl 3-hydroxy-5-methoxyphthalate;24953-74-0;Dimethyl 3-hydroxy-5-methoxybenzene-1,2-dicarboxylate;SCHEMBL20812825;DTXSID30564807;Dimethyl3-hydroxy-5-methoxyphthalate

Chemical Property of Dimethyl 3-hydroxy-5-methoxyphthalate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 240.06338810
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

≥99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)O)C(=O)OC)C(=O)OC

Technology Process of Dimethyl 3-hydroxy-5-methoxyphthalate

There total 4 articles about Dimethyl 3-hydroxy-5-methoxyphthalate 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: 19.7%

3-methoxycyclohex-2-en-1-one (16807-60-6) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 3-hydroxy-5-methoxyphthalate (24953-74-0)

Guidance literature:

3-methoxycyclohex-2-en-1-one; With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 15h; Inert atmosphere;

With chloro-trimethyl-silane; In tetrahydrofuran; at 0 ℃; for 0.25h;

dimethyl acetylenedicarboxylate; In tetrahydrofuran; at -78 - 50 ℃; for 2h;

Reference yield:

(5,5-dimethylcyclohexa-1,3-diene-1,3-diyl)bis(oxy)bis(trimethylsilane) (63559-15-9) → dimethyl 3-hydroxy-5-methoxyphthalate (24953-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: neat (no solvent) / 120 °C / Inert atmosphere

2: potassium carbonate / Inert atmosphere

With potassium carbonate; In neat (no solvent); 1: |Alder-Rickert Cycloaddition;

DOI:10.1016/j.tet.2018.02.048

Reference yield:

3,5-Dihydroxy-phthalic acid dimethyl ester (67609-51-2) + dimethyl sulfate (77-78-1) → dimethyl 3-hydroxy-5-methoxyphthalate (24953-74-0)

Guidance literature:

With potassium carbonate; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2018.02.048

upstream raw materials:

Dimethyl 3,5-dimethoxyphthalate

3-methoxycyclohex-2-en-1-one

dimethyl acetylenedicarboxylate

3,5-Dihydroxy-phthalic acid dimethyl ester

Downstream raw materials:

5-Methoxy-3-methoxymethoxy-phthalic acid dimethyl ester

Refernces

• 1、 -. "AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION". Page/Page column 479. . Retrieved 2017/12/01.