Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester

Base Information

• Chemical Name: Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester
• CAS No.: 1026342-97-1
• Molecular Formula: C₂₇H₃₈O₈S₂
• Molecular Weight: 554.726

Synonyms:

Chemical Property of Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester

There total 11 articles about Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl 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:

trans-3-(3,5-dimethoxyphenyl)-2-propen-1-ol (147663-61-4,29584-66-5) → Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester (1026342-97-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2 min, 2.) CH₂Cl₂, 5 min

3: 82 percent / propionic acid / 3 h / 140 °C

4: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

5: Ph₃P, CBr₄ / diethyl ether / 8 h / Ambient temperature

6: 88 percent / DMSO / 2 h / 50 °C

7: 63 percent / DIBAL-H / benzene / 14 h / Ambient temperature

8: 88 percent / 1.92M t-BuLi / 1.) pentane, ether, -78 deg C, 45 min, 2.) ether, r.t., 8 h

9: 96 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

10: Et₃N / diethyl ether / 10 h

With lithium aluminium tetrahydride; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo00079a045

Reference yield:

(E)-ethyl 3-(3,5-dimethoxyphenyl)acrylate (42174-79-8,29584-64-3) → Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester (1026342-97-1)

Guidance literature:

Multi-step reaction with 11 steps

1: LiAlH₄ / tetrahydrofuran / 6 h / Heating

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2 min, 2.) CH₂Cl₂, 5 min

4: 82 percent / propionic acid / 3 h / 140 °C

5: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

6: Ph₃P, CBr₄ / diethyl ether / 8 h / Ambient temperature

7: 88 percent / DMSO / 2 h / 50 °C

8: 63 percent / DIBAL-H / benzene / 14 h / Ambient temperature

9: 88 percent / 1.92M t-BuLi / 1.) pentane, ether, -78 deg C, 45 min, 2.) ether, r.t., 8 h

10: 96 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

11: Et₃N / diethyl ether / 10 h

With lithium aluminium tetrahydride; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo00079a045

Reference yield:

3-(3,5-dimethoxyphenyl)-1-propanal (125187-47-5) → Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-1-methanesulfonyloxy-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester (1026342-97-1)

Guidance literature:

Multi-step reaction with 9 steps

2: 82 percent / propionic acid / 3 h / 140 °C

3: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

4: Ph₃P, CBr₄ / diethyl ether / 8 h / Ambient temperature

5: 88 percent / DMSO / 2 h / 50 °C

6: 63 percent / DIBAL-H / benzene / 14 h / Ambient temperature

7: 88 percent / 1.92M t-BuLi / 1.) pentane, ether, -78 deg C, 45 min, 2.) ether, r.t., 8 h

8: 96 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

9: Et₃N / diethyl ether / 10 h

With lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo00079a045

upstream raw materials:

methanesulfonyl chloride

(+/-)-(E)-8-(3,5-Dimethoxyphenyl)-1-(3,5-dimethyl-4-hydroxyphenyl)-5-methyl-5-octen-1-ol

trans-3-(3,5-dimethoxyphenyl)-2-propen-1-ol

(E)-ethyl 3-(3,5-dimethoxyphenyl)acrylate

Downstream raw materials:

(+/-)-(E)-1-(3,5-Dimethoxyphenyl)-8-(3,5-dimethyl-4-hydroxyphenyl)-4-methyl-3-octene

4-[(E)-8-(3,5-Dimethoxy-phenyl)-5-methyl-oct-5-enylidene]-2,6-dimethyl-cyclohexa-2,5-dienone

Methanesulfonic acid 4-[(E)-8-(3,5-dimethoxy-phenyl)-5-methyl-oct-5-enyl]-2,6-dimethyl-phenyl ester

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