1-Menthoxy-1-butyne

Base Information

• Chemical Name: 1-Menthoxy-1-butyne
• CAS No.: 108266-28-0
• Molecular Formula: C14H24 O
• Molecular Weight: 208.33976
• Mol file: 108266-28-0.mol

Synonyms:Cyclohexane,2-(1-butynyloxy)-4-methyl-1-(1-methylethyl)-, (1S,2R,4R)- (9CI); Cyclohexane,2-(1-butynyloxy)-4-methyl-1-(1-methylethyl)-, [1S-(1a,2b,4b)]-

Chemical Property of 1-Menthoxy-1-butyne

Chemical Property:

• PSA: 9.23000
• LogP: 3.83470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Menthoxy-1-butyne

There total 3 articles about 1-Menthoxy-1-butyne 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: 93.0%

ethynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether (108167-50-6) + ethyl iodide (75-03-6) → [1S-[1α,2β,4β]]-2-(1-butynyloxy)-4-methyl-1-(1-methylethyl)cyclohexane (108266-28-0)

Guidance literature:

ethynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - -40 ℃; for 1h; Inert atmosphere;

ethyl iodide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.15227/orgsyn.074.0013

Reference yield:

(-)-menthol (2216-51-5) → [1S-[1α,2β,4β]]-2-(1-butynyloxy)-4-methyl-1-(1-methylethyl)cyclohexane (108266-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydride / tetrahydrofuran / 0.33 h / Inert atmosphere

1.2: 1 h / -50 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -40 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With n-butyllithium; potassium hydride; In tetrahydrofuran; hexane;

DOI:10.15227/orgsyn.074.0013

Reference yield:

Trichloroethylene (79-01-6) + (-)-menthol (2216-51-5) + ethyl iodide (75-03-6) → [1S-[1α,2β,4β]]-2-(1-butynyloxy)-4-methyl-1-(1-methylethyl)cyclohexane (108266-28-0)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00389a048

upstream raw materials:

Trichloroethylene

(-)-menthol

ethyl iodide

ethynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether

Refernces

• 1、 Moyano, Albert,Charbonnier, Florence,Greene, Andrew E.. "A Simple Preparation of Chiral Acetylenic Ethers". . p. 2919 - 2922. Retrieved 2007/10/02.