(+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate

Base Information

• Chemical Name: (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate
• CAS No.: 66348-55-8
• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.381
• Mol file: 66348-55-8.mol

Synonyms:

Chemical Property of (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate

There total 21 articles about (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol 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: 42.0%

1-iodo-3-methyl-5-acetoxy-2-pentene (104543-25-1,104543-26-2) → (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate (66348-55-8,64309-04-2)

Guidance literature:

In nitromethane; for 96h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91411-5

Reference yield:

ethyl 3-methyl-6-(1,1-ethylenedioxyethyl)-2,4(E),9-decatrienoate → (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate (66348-55-8,64309-04-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / (PhCO₂Me)Cr(CO)3 / acetone / 3.5 h / 120 - 125 °C / 60800 Torr

2: LiAlH₄ / diethyl ether / 0.5 h

3: 1.0 g / oxalic acid, H₂O / acetone / 3 h / Heating

4: tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C

5: 112 mg / Na₂CO₃ / 1 h / 100 °C

With lithium aluminium tetrahydride; water; hydrogen; oxalic acid; sodium carbonate; methyl benzoate*Cr(CO)3; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; acetone;

DOI:10.1007/BF00707233

Reference yield:

(Z)-5-chloro-3-methyl-pent-3-en-1-ol (39149-98-9) → (+/-)-(Z)-3-methyl-6-isopropenyl-3,9-decadien-1-ol acetate (66348-55-8,64309-04-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / aq.HCl / CH₂Cl₂ / 1.5 h / 25 °C

2: 72 percent / NaBr / various solvent(s) / 3 h / 25 °C

4: 86 percent / glacial acetic acid / 26 h / 90 °C

5: K₂CO₃ / methanol / 0.5 h / 25 °C

6: aq.NaOH / ethanol / 24 h / Heating; pH 9-10

7: 92 percent / pyridine / 0.58 h / 25 °C

8: 2.) Ac₂O / 1.) THF, 0.5 h, 2.) pyridine, 25 deg C, 0.5 h

With pyridine; hydrogenchloride; sodium hydroxide; acetic anhydride; potassium carbonate; acetic acid; sodium bromide; In methanol; ethanol; dichloromethane;

DOI:10.1021/jo00146a025

upstream raw materials:

5-Isopropenyl-2-methyl-nona-1,8-dien-3-ol

acetic anhydride

(Z)-undec-2-en-4-ol

formaldehyd