(E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Base Information

• Chemical Name: (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester
• CAS No.: 182010-93-1
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 182010-93-1.mol

Synonyms:(E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Chemical Property of (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

There total 7 articles about (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic 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)-6-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3,4-dimethyl-phenyl]-4-methyl-hex-4-enoic acid methyl ester → (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester (182010-93-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.166667h;

DOI:10.1021/jm9603633

Reference yield:

2,3-dimethyl-1,4-dihydroxybenzene (608-43-5) → (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester (182010-93-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 35 percent / K₂CO₃ / dimethylformamide / Ambient temperature

2: imidazole / dimethylformamide

3: N,N-diethylaniline / 4 h / 200 °C

4: aq. NaOH / dimethylformamide / 1 h

5: 1.) pyridine, ozonized O₂, 2.) Me₃S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, RT, overnight

6: tetrahydrofuran / -78 °C

7: pivalic acid / Heating

8: 1.0 M tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

With pyridine; 1H-imidazole; sodium hydroxide; ozone-containing oxygen; trimethylsulfonium; tetrabutyl ammonium fluoride; potassium carbonate; N,N-diethylaniline; Trimethylacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm9603633

Reference yield:

(4-Allyloxy-2,3-dimethyl-phenoxy)-tert-butyl-dimethyl-silane (1025823-67-9) → (E)-6-(5-Hydroxy-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester (182010-93-1)

Guidance literature:

Multi-step reaction with 6 steps

1: N,N-diethylaniline / 4 h / 200 °C

2: aq. NaOH / dimethylformamide / 1 h

3: 1.) pyridine, ozonized O₂, 2.) Me₃S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, RT, overnight

4: tetrahydrofuran / -78 °C

5: pivalic acid / Heating

6: 1.0 M tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

With pyridine; sodium hydroxide; ozone-containing oxygen; trimethylsulfonium; tetrabutyl ammonium fluoride; N,N-diethylaniline; Trimethylacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm9603633

upstream raw materials:

2,3-dimethyl-1,4-dihydroxybenzene

(4-Allyloxy-2,3-dimethyl-phenoxy)-tert-butyl-dimethyl-silane

6-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dimethyl-phenol

(5-Allyl-4-methoxy-2,3-dimethyl-phenoxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(E)-6-(5-Cyano-2-methoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

(E)-6-(2,5-Dimethoxy-3,4-dimethyl-phenyl)-4-methyl-hex-4-enoic acid methyl ester

(E)-6-(2-Methoxy-3,4-dimethyl-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-hex-4-enoic acid methyl ester