(S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol

Base Information

• Chemical Name: (S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol
• CAS No.: 79547-82-3
• Molecular Formula: C21H16O2
• Molecular Weight: 300.357
• Mol file: 79547-82-3.mol

Synonyms:[1,1'-Binaphthalen]-2-ol,2'-methoxy-, (R)-;(R)-2-Hydroxy-2'-methoxy-1,1'-binaphthyl;2'-Methoxy-1,1'-binaphthalen-2-ol;1-(2-methoxynaphthalen-1-yl)naphthalen-2-ol;

Chemical Property of (S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 107-109℃
• Refractive Index: 1.711
• Boiling Point: 435.28 °C at 760 mmHg
• Flash Point: 227.213 °C
• PSA: 69.92000
• Density: 1.224 g/cm³
• LogP: 1.26600
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

(R)-(+)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol 97+%, 99%ee ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol

There total 6 articles about (S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol 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:

benzyl bromide (100-39-0) + 2-hydroxy-2'-methoxy-1,1'-binaphthyl (35193-70-5) → (S)-2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene + 2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene + (Ra)-1-(2-methoxynaphthalen-1-yl)naphthalen-2-ol (79547-82-3)

Guidance literature:

With potassium phosphate; N-benzylquinidinium chloride; In water; toluene; at 24.84 ℃; for 18h; Reagent/catalyst; enantioselective reaction; Resolution of racemate;

DOI:10.1002/anie.201814381

Reference yield:

2-hydroxy-2'-methoxy-1,1'-binaphthyl (35193-70-5) + iodomethylbenzene (620-05-3) → (S)-2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene + 2-(benzyloxy)-2'-methoxy-1,1'-binaphthalene + (Ra)-1-(2-methoxynaphthalen-1-yl)naphthalen-2-ol (79547-82-3)

Guidance literature:

With potassium phosphate; C₂₇H₂₈F₅N₂O₂⁽¹⁺⁾*Br^(1-); In water; toluene; at 24.84 ℃; for 48h; Reagent/catalyst; Solvent; enantioselective reaction; Resolution of racemate;

DOI:10.1002/anie.201814381

Reference yield:

2,2-diphenylacetic pivalic anhydride + 2-hydroxy-2'-methoxy-1,1'-binaphthyl (35193-70-5) → C35H26O3 + C35H26O3 + (Ra)-1-(2-methoxynaphthalen-1-yl)naphthalen-2-ol (79547-82-3) + (S)-2-methoxy-2′-hydroxy-1,1′-binaphthyl

Guidance literature:

With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In chloroform; at 20 - 25 ℃; for 18h; regioselective reaction;

DOI:10.1002/chem.201805631

upstream raw materials:

2-hydroxy-2'-methoxy-1,1'-binaphthyl

1,1'-bi-2-naphthol

benzyl bromide

benzyl tosylate

Refernces

• 1、 Jones, Benjamin A.,Balan, Tudor,Jolliffe, John D.,Campbell, Craig D.,Smith, Martin D.. "Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion". supporting information. p. 4596 - 4600. Retrieved 2019/03/13.