4-(6-Methoxynaphthalen-2-yl)butan-2-ol

Base Information

• Chemical Name: 4-(6-Methoxynaphthalen-2-yl)butan-2-ol
• CAS No.: 65726-24-1
• Molecular Formula: C15H18O2
• Molecular Weight: 230.307
• Hs Code.: 2909499000
• UNII: 394320Y6J8
• Nikkaji Number: J1.454.956K
• Wikidata: Q27256851
• ChEMBL ID: CHEMBL3278702
• Mol file: 65726-24-1.mol

Synonyms:4-(6-methoxynaphthalen-2-yl)butan-2-ol;65726-24-1;Nabumetone alcohol;4-(2-methoxynaphthalen-6-yl)butan-2-ol;Nabumetone alcohol, (+/-)-;(2RS)-4-(6-Methoxynaphthalen-2-yl)butan-2-ol;Nabumetone impurity C [EP];4-(6'-Methoxy-2'-naphthyl)-butan-2-ol;UNII-394320Y6J8;394320Y6J8;2-Naphthalenepropanol, 6-methoxy-alpha-methyl-;Nabumetone impurity, 4-(6'-methoxy-2'-naphthyl)-butan-2-ol- [USP];Nabumetone Imp. C (EP);Nabumetone Impurity C;SCHEMBL8338309;CHEMBL3278702;JNVOSYBERVWSGY-UHFFFAOYSA-N;AMY10500;AKOS015151980;4-(6-Methoxy-2-naphthyl)-2-butanol;4-(6-methoxy-2-naphthyl)-butan-2-ol;2-hydroxy-4-(6-methoxy-2-naphthyl)butane;NABUMETONE IMPURITY C [EP IMPURITY];2-hydroxy-4-(6-methoxy-2-naphthyl) butane;FT-0713836;L10108;EN300-1851210;Q27256851;2-NAPHTHALENEPROPANOL, 6-METHOXY-.ALPHA.-METHYL-;NABUMETONE IMPURITY, 4-(6'-METHOXY-2'-NAPHTHYL)-BUTAN-2-OL- [USP IMPURITY]

Chemical Property of 4-(6-Methoxynaphthalen-2-yl)butan-2-ol

Chemical Property:

• Melting Point: 99-100 °C
• Boiling Point: 390.5±17.0 °C(Predicted)
• PKA: 15.11±0.20(Predicted)
• PSA: 29.46000
• Density: 1.090
• LogP: 3.16180
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 230.130679813
• Heavy Atom Count: 17
• Complexity: 229

Purity/Quality:

98%min ^*data from raw suppliers

2-HydroxyNabumetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC1=CC2=C(C=C1)C=C(C=C2)OC)O
• Uses: 2-Hydroxy Nabumetone is derived from Nabumetone (N200500), which is an anti-inflammatory and antibacterial agent (1) and a non-steroidal anti-inflammatory prodrug used for treatment of inflammatory and degenerative rheumatic diseases.

Technology Process of 4-(6-Methoxynaphthalen-2-yl)butan-2-ol

There total 2 articles about 4-(6-Methoxynaphthalen-2-yl)butan-2-ol 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: 65.0%

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one (73356-31-7,218768-11-7) → 4-(6-methoxynaphthalen-2-yl)butan-2-ol (65726-24-1) + nabumetone (42924-53-8) + (±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone (220786-56-1,98386-83-5)

Guidance literature:

With sulfuric acid; palladium 10% on activated carbon; hydrogen; In ethyl acetate;

DOI:10.1021/op980060d

Reference yield:

6-methoxy-2-acetylnaphthalene (3900-45-6) → 4-(6-methoxynaphthalen-2-yl)butan-2-ol (65726-24-1) + nabumetone (42924-53-8) + (±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone (220786-56-1,98386-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium sec-butoxide / dimethyl sulfoxide / 1 h / 50 - 60 °C

1.2: pH 2

2.1: hydrogen; palladium 10% on activated carbon; sulfuric acid / ethyl acetate

With sulfuric acid; palladium 10% on activated carbon; hydrogen; potassium sec-butoxide; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/op980060d

Reference yield: 11.0%

C9H10ClO2P (936616-27-2) + 4-(6-methoxynaphthalen-2-yl)butan-2-ol (65726-24-1) → 2-[3-(6-methoxynaphthalen-2-yl)-1-methylpropoxy]-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

Guidance literature:

C₉H₁₀ClO₂P; 4-(6-methoxynaphthalen-2-yl)butan-2-ol; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 24 ℃; for 20h;

With tert.-butylhydroperoxide; In acetonitrile; at 0 - 24 ℃; for 4h; Further stages.;

DOI:10.1007/s11095-006-9187-y

upstream raw materials:

6-methoxy-2-acetylnaphthalene

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one

Downstream raw materials:

3,4,5-Trimethoxy-benzoic acid 3-(6-methoxy-naphthalen-2-yl)-1-methyl-propyl ester

Refernces