5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene

Base Information

• Chemical Name: 5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene
• CAS No.: 184221-88-3
• Molecular Formula: C₃₆H₃₀O₄
• Molecular Weight: 526.632
• DSSTox Substance ID: DTXSID101195760
• Mol file: 184221-88-3.mol

Synonyms:DTXSID101195760;5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene;184221-88-3

Chemical Property of 5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene

Chemical Property:

• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 526.21440943
• Heavy Atom Count: 40
• Complexity: 683

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC2=C(C=CC(=C21)OCC3=CC=CC=C3)C4=C5C=CC=C(C5=C(C=C4)OCC6=CC=CC=C6)OC

Technology Process of 5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene

There total 3 articles about 5,5'-Dimethoxy-4,4'-bis(phenylmethoxy)-1,1'-binaphthalene 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:

8-methoxy-naphthalen-1-ol (3588-75-8) → 4,4'-Bis-benzyloxy-5,5'-dimethoxy-[1,1']binaphthalenyl (184221-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH, Br₂ / CCl₄ / 0.25 h / Ambient temperature

2: 100 percent / NaH / dimethylformamide / 36 h / Ambient temperature

3: 1) n-BuLi, B(OMe)3, 2) Na₂CO₃ / 2) Pd(PPh₃)4 / 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H₂O, toluene, reflux, 24 h

With n-butyllithium; Trimethyl borate; bromine; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9617880

Reference yield:

4-bromo-8-methoxynaphthalen-1-ol (184221-86-1) → 4,4'-Bis-benzyloxy-5,5'-dimethoxy-[1,1']binaphthalenyl (184221-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide / 36 h / Ambient temperature

2: 1) n-BuLi, B(OMe)3, 2) Na₂CO₃ / 2) Pd(PPh₃)4 / 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H₂O, toluene, reflux, 24 h

With n-butyllithium; Trimethyl borate; sodium hydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

DOI:10.1021/jo9617880

Reference yield:

4-Benzyloxy-1-bromo-5-methoxy-naphthalene (184221-87-2) → 4,4'-Bis-benzyloxy-5,5'-dimethoxy-[1,1']binaphthalenyl (184221-88-3)

Guidance literature:

With n-butyllithium; Trimethyl borate; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h;

DOI:10.1021/jo9617880

upstream raw materials:

4-Benzyloxy-1-bromo-5-methoxy-naphthalene

8-methoxy-naphthalen-1-ol

4-bromo-8-methoxynaphthalen-1-ol