(2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate

Base Information

• Chemical Name: (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate
• CAS No.: 85785-72-4
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 85785-72-4.mol

Synonyms:

Chemical Property of (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate

There total 19 articles about (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate 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: 90.0%

acetic anhydride (108-24-7) + (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadien-1-ol (85785-71-3,91878-58-9,94346-66-4,94347-30-5,99529-47-2,99529-69-8) → (2EZ,4E,1'R,2'R,6'R)-(-)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate (85785-72-4,91878-59-0,94346-67-5,94347-31-6,99529-48-3,99529-70-1)

Guidance literature:

With pyridine; for 30h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield: 87.7%

acetic anhydride (108-24-7) + (+/-)-(2EZ,4E)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadien-1-ol (85785-71-3,91878-58-9,94346-66-4,94347-30-5,99529-47-2,99529-69-8) → (+/-)-(2EZ,4E)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate (85785-72-4,91878-59-0,94346-67-5,94347-31-6,99529-48-3,99529-70-1)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/S0040-4020(01)96890-5

Reference yield:

3-methylpent-2-en-4-yn-1-ol (6153-06-6,105-29-3) → (+/-)-(2EZ,4E)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadienyl acetate (85785-72-4,91878-59-0,94346-67-5,94347-31-6,99529-48-3,99529-70-1)

Guidance literature:

Multi-step reaction with 7 steps

1: p-TsOH_.H₂O / diethyl ether / 0 - 25 °C

3: 1.7 g / NaH / benzene / 2 h / 10 °C

4: 1.) LiNPr₂; 2.) HMPA / 1.) THF, -20 deg C, 20 min; 2.) -20 deg C, 1.5 h

5: 1.0 g / 2percent NaOH / H₂O / 4 h / Heating

6: 98.6 percent / acetic acid; tetrahydrofuran; H₂O / 3 h / 40 - 50 °C

7: 87.7 percent / pyridine / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium di-n-propylamide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; water; acetic acid; benzene;

DOI:10.1016/S0040-4020(01)96890-5

upstream raw materials:

acetic anhydride

(+/-)-(2EZ,4E)-5-(1',2',6'-trimethyl-3'-oxocyclohexyl)-3-methyl-2,4-pentadien-1-ol

3-methylpent-2-en-4-yn-1-ol

(E)-tetrahydro-2-<(3-methyl-2-penten-4-ynyl)oxy>-2H-pyran

Downstream raw materials:

3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-((6R,7R,8R)-6,7,8-trimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-penta-2,4-dienyl]-benzaldehyde

(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

(2'E,4'E,1''R,2''R,6''R)-4-chloro-2-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol

(2'E,4'E,1''R,2''R,6''R)-3-<5'-(3'',3''-ethylenedioxy-1'',2'',6''-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene