2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol

Base Information

• Chemical Name: 2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol
• CAS No.: 109028-15-1
• Molecular Formula: C15H24 O2
• Molecular Weight: 236.354
• Mol file: 109028-15-1.mol

Synonyms:Benzenepentanol,2-hydroxy-a,a,e,4-tetramethyl-, (S)-; (+)-Curcudiol; (S)-(+)-Curcudiol; Curcudiol

Chemical Property of 2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol

Chemical Property:

• Vapor Pressure: 2.55E-05mmHg at 25°C
• Boiling Point: 344.2°Cat760mmHg
• Flash Point: 154°C
• Density: 1.008g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol

There total 42 articles about 2-[(2S)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol 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: 75.0%

methyl magnesium iodide (917-64-6) + (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester (170423-76-4) → (S)-2-(6-hydroxy-6-methylheptan-2-yl)-5-methylphenol (109028-15-1)

Guidance literature:

In tetrahydrofuran;

DOI:10.1055/s-1998-1844

Reference yield: 62.0%

(S)-curcuphenol (70878-71-6) → (S)-2-(6-hydroxy-6-methylheptan-2-yl)-5-methylphenol (109028-15-1)

Guidance literature:

(S)-curcuphenol; With mercury(II) diacetate; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;

With sodium hydroxide; In tetrahydrofuran; water; for 0.0166667h;

With sodium tetrahydroborate; In tetrahydrofuran; water; for 0.333333h;

DOI:10.1021/ol2022214

Reference yield:

(E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester (164921-78-2) → (S)-2-(6-hydroxy-6-methylheptan-2-yl)-5-methylphenol (109028-15-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: immobilized lipase (MY-30); H₂O / diisopropyl ether / 72 h / 33 °C

2.1: H₂ / 20 percent Pd(OH)2-C / ethyl acetate / 20 °C

3.1: pyridine / 12 h / 20 °C

4.1: 40 percent / NaBH₄ / dimethylsulfoxide / 2 h / 80 °C

5.1: 48 percent / Ph₃P; I₂; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C

6.1: 99 percent / dimethylformamide / 12 h / 20 °C

7.1: 2 M aq. NaOH / ethanol / 12 h / Heating

7.2: 54 percent / diethyl ether

8.1: AlCl₃; EtSH / 1 h / 0 °C

9.1: diethyl ether / 48 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; aluminium trichloride; immobilized lipase (MY-30); water; hydrogen; iodine; triphenylphosphine; ethanethiol; palladium hydroxide - carbon; In diethyl ether; ethanol; di-isopropyl ether; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.49.1581

upstream raw materials:

methyl magnesium iodide

(S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester

(E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester

(S)-1-[5-(benzyloxy)pentan-2-yl]-2-methoxy-4-methylbenzene

Downstream raw materials:

4-nitrocurcudiol

2,4-dinitrocurcudiol