(1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde

Base Information

• Chemical Name: (1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde
• CAS No.: 216978-80-2
• Molecular Formula: C₂₅H₂₂O₅
• Molecular Weight: 402.447
• DSSTox Substance ID: DTXSID001165221
• Nikkaji Number: J1.053.437B,J3.532.096B
• Mol file: 216978-80-2.mol

Synonyms:216978-80-2;(1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde;3-(methoxymethoxy)-4-[2-(methoxymethoxy)naphthalen-1-yl]naphthalene-2-carbaldehyde;2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carbaldehyde;(1R)-2,2'-Bis(methoxymethoxy)[1,1'-binaphthalene]-3-carboxaldehyde;[1,1'-Binaphthalene]-3-carboxaldehyde, 2,2'-bis(methoxymethoxy)-, (1R)-;1000069-41-9;SCHEMBL12588892;DTXSID001165221;(S)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde;R-2,2'-bis(methoxymethoxy)-[1,1'-Binaphthalene]-3-carboxaldehyde;CS-0087953;(R)-2,2'-Bis(methoxymethoxy)-1,1'-binaphthalenyl-3-carbaldehyde

Chemical Property of (1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 402.14672380
• Heavy Atom Count: 30
• Complexity: 540

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COCOC1=C(C2=CC=CC=C2C=C1)C3=C(C(=CC4=CC=CC=C43)C=O)OCOC

Technology Process of (1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde

There total 3 articles about (1R)-2,2'-Bis(methoxymethoxy)-[1,1'-binaphthalene]-3-carboxaldehyde 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: 76.0%

rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene (173831-50-0) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde (349149-07-1,1000069-41-9,216978-80-2)

Guidance literature:

rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1.16667h; Further stages.;

DOI:10.1021/ja993650f

Reference yield: 67.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) → (R,R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthol-3-carboxyaldehyde (1000069-41-9,216978-80-2,349149-07-1)

Guidance literature:

(R,R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthol; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at -78 - 0 ℃; for 0.5h;

N,N-dimethyl-formamide; at -78 - 0 ℃; for 1.16667h;

Reference yield:

1,1'-bi-2-naphthol (602-09-5) → (S)/(R)-1,1'-binaphthalene-2,2-bis(methoxymethyloxy)-3-carbaldehyde (349149-07-1,1000069-41-9,216978-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / NaH / tetrahydrofuran / 4 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2.2: 70 percent / tetrahydrofuran; various solvent(s) / 4 h / 20 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0957-4166(02)00571-2

upstream raw materials:

rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene

N,N-dimethyl-formamide

1,1'-bi-2-naphthol

Downstream raw materials:

tricarbonyl(η(6)-toluene)chromium

3,3''-(oxydimethylene)-di-1,1'-bi-2-naphthol

(R)-2,2'-dihydroxy-[1,1']-binaphthyl-3-carbaldehyde