carveol methyl ether

Base Information

• Chemical Name: carveol methyl ether
• CAS No.: 57022-47-6
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.263
• Mol file: 57022-47-6.mol

Synonyms:carveol methyl ether

Chemical Property of carveol methyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carveol methyl ether

There total 11 articles about carveol methyl ether 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: 80.0%

(2S,4S)-carveol (7632-16-8,22567-18-6,20307-86-2) + methyl iodide (74-88-4) → (4S,6S)-4-Isopropenyl-6-methoxy-1-methyl-cyclohexene (57022-47-6,57089-64-2,69744-18-9,141783-50-8)

Guidance literature:

(2S,4S)-carveol; With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 2h; Inert atmosphere;

methyl iodide; In dimethyl sulfoxide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.1c01879

Reference yield:

methanol (67-56-1) + (2S,4S)-carveol (7632-16-8,22567-18-6,20307-86-2) → (4S,6S)-4-Isopropenyl-6-methoxy-1-methyl-cyclohexene (57022-47-6,57089-64-2,69744-18-9,141783-50-8) + pinol (2437-97-0,89576-52-3) + (4S,6R)-4-Isopropenyl-6-methoxy-1-methyl-cyclohexene

Guidance literature:

With cerium(III) chloride; for 20h; Title compound not separated from byproducts; Heating;

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (4S,6S)-4-Isopropenyl-6-methoxy-1-methyl-cyclohexene (57022-47-6,57089-64-2,69744-18-9,141783-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

2.1: sodium hydride / dimethyl sulfoxide / 2 h / 60 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/acs.orglett.1c01879

upstream raw materials:

1,2,8-tribromo-p-menthane

sodium methylate

methanol

(+)-trans-carveyl acetate

Downstream raw materials:

((S)-5-Isopropenyl-2-methyl-cyclohex-2-enyl)-benzene

(R,S)-trans-2-Methyl-3-phenyl-5-isopropenyl-1-cyclohexene

Carvone

trans-carveol acetate

Refernces

• 1、 Uzarewicz,Dresler. "Reaction of cyclic allylic acetates with aliphatic alcohols in the presence of cerium(III) chloride". . p. 1921 - 1930. Retrieved 2007/10/03.