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

Base Information

• Chemical Name: (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester
• CAS No.: 170423-76-4
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.311
• Mol file: 170423-76-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 23 articles about (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester 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:

(E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester (164921-78-2) → (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester (170423-76-4)

Guidance literature:

Multi-step reaction with 8 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

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

Reference yield:

methyl (4S)-(2-methoxy-4-methylpenyl)-5-hydroxypentanoate (170423-66-2) → (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester (170423-76-4)

Guidance literature:

Multi-step reaction with 7 steps

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

2.1: pyridine / 12 h / 20 °C

3.1: 40 percent / NaBH₄ / dimethylsulfoxide / 2 h / 80 °C

4.1: 48 percent / Ph₃P; I₂; imidazole / diethyl ether; acetonitrile / 0.5 h / 20 °C

5.1: 99 percent / dimethylformamide / 12 h / 20 °C

6.1: 2 M aq. NaOH / ethanol / 12 h / Heating

6.2: 54 percent / diethyl ether

7.1: AlCl₃; EtSH / 1 h / 0 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; aluminium trichloride; hydrogen; iodine; triphenylphosphine; ethanethiol; palladium hydroxide - carbon; In diethyl ether; ethanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.49.1581

Reference yield:

methyl 4-(2'-methoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate (164921-74-8) → (S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester (170423-76-4)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine

2: H₂O / diisopropyl ether / immobilized lipase MY-30 from Candida cylindracea

3: H₂ / Pd(OH)2/C

4: pyridine

5: 40 percent / NaBH₄ / dimethylsulfoxide

6: 48 percent / I₂/PPh₃

7: 99 percent / dimethylformamide

8: NaOH/EtOH

10: EtSH/AlCl₃

With pyridine; sodium hydroxide; sodium tetrahydroborate; aluminium trichloride; ethanol; water; hydrogen; iodine; triphenylphosphine; ethanethiol; palladium dihydroxide; In di-isopropyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0957-4166(95)00229-I

upstream raw materials:

methyl-(5S)-(2-methoxy-4-methylphenyl)hexanoate

diazomethane

(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:

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