4(RS),8(S)-dimethyldecanal dimethyl acetal

Base Information

• Chemical Name: 4(RS),8(S)-dimethyldecanal dimethyl acetal
• CAS No.: 87106-39-6
• Molecular Formula: C₁₄H₃₀O₂
• Molecular Weight: 230.391
• Mol file: 87106-39-6.mol

Synonyms:

Chemical Property of 4(RS),8(S)-dimethyldecanal dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(RS),8(S)-dimethyldecanal dimethyl acetal

There total 34 articles about 4(RS),8(S)-dimethyldecanal dimethyl acetal 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: 84.0%

lithium dimethylcuprate (15681-48-8) + Toluene-4-sulfonic acid (2R,6S)-9,9-dimethoxy-2,6-dimethyl-nonyl ester (108864-08-0) → (4R,8R)-1,1-Dimethoxy-4,8-dimethyl-decane (87106-39-6,87118-43-2,97271-12-0,97271-13-1,106445-80-1,108943-54-0)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0040-4039(00)85003-0

Reference yield: 74.0%

6-benzenesulfonyl-1,1-dimethoxy-4,8-dimethyldecane (132723-91-2,132830-30-9,132830-31-0,132830-32-1) → 4,8-dimethyldecanal dimethylacetal (87106-39-6)

Guidance literature:

With lithium ethylamide; In tetrahydrofuran; for 1h;

Reference yield:

5-iodomethyl-2,2-dimethyl-1,3-dioxane (97827-17-3) → (4R,8R)-1,1-Dimethoxy-4,8-dimethyl-decane (87106-39-6,87118-43-2,97271-12-0,97271-13-1,106445-80-1,108943-54-0)

Guidance literature:

Multi-step reaction with 10 steps

2: 77 percent / 1N HCl / tetrahydrofuran

3: 1.) trimethylsilyl chloride, NaI, CH₂Cl₂ 2.) 30percent H₂O₂, AcOH

4: 91 percent / FeSO₄, Cu(OAc)2 / methanol

5: 95 percent / Bu₃SnCl, AIBN, 1.5 eq. NaBH₄

6: 53 percent / DIBAL

7: 78 percent / pTSOH

8: 77 percent / H₂ / PtO₂

9: 70 percent

10: 84 percent / diethyl ether

With hydrogenchloride; sodium tetrahydroborate; copper diacetate; 2,2'-azobis(isobutyronitrile); tributyltin chloride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; iron(II) sulfate; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)85003-0

upstream raw materials:

lithium dimethylcuprate

Toluene-4-sulfonic acid (2R,6S)-9,9-dimethoxy-2,6-dimethyl-nonyl ester

5-iodomethyl-2,2-dimethyl-1,3-dioxane

(2S,6R)-9,9-Dimethoxy-2,6-dimethyl-nonan-1-ol

Refernces

• 1、 Mori, Kenji,Takikawa, Hirosato. "Pheromone Synthesis, CXXX. Synthesis of (4S,8S)- and (4S,8R)-4,8-Dimethyldecanal, the Stereoisomers of the Aggregation Pheromone of Tribolium castaneum". . p. 497 - 500. Retrieved 2007/10/02.
• 2、 Randad, R. S.,Kulkarni, G. H.. "Synthesis of 4(RS),8(S)-Dimethyldecanal: An Aggrigation Pheromone of Red Flour Beetles". . p. 296 - 298. Retrieved 2007/10/02.