ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate

Base Information

• Chemical Name: ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate
• CAS No.: 139932-51-7
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• Mol file: 139932-51-7.mol

Synonyms:

Chemical Property of ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate

There total 8 articles about ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate 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: 95.0%

methyl-triphenylphosphonium iodide (2065-66-9) + ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-oxocyclohexancarboxylate (139932-54-0,139932-58-4) → ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate (139932-51-7,139932-52-8)

Guidance literature:

With sodium tert-pentoxide; In toluene; for 2h; Heating;

DOI:10.1080/00397919208019254

Reference yield:

4-carbethoxy-3-methyl-2-cyclohexen-1-one (487-51-4) → ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate (139932-51-7,139932-52-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / t-BuOK / 2-methyl-propan-2-ol

2: 88 percent / CuI, BF₃*Et₂O / diethyl ether / 1.) -50 deg C, 5 min, 2.) -30 deg C, 75 min

3: 85 percent / sodium 2,2-dimethylpropanolate / toluene / 1.) 25 deg C, 20 min, 2.) reflux, 2 h

4: 1.) Bu₃SnH, AIBN, 2.) aq. KF / 1.) benzene, reflux, 13 h, 2.) ether, 10 h

With potassium fluoride; copper(l) iodide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; potassium tert-butylate; tri-n-butyl-tin hydride; sodium tert-pentoxide; In diethyl ether; toluene; tert-butyl alcohol;

Reference yield:

ethyl 3-(β-phenylethyl)-2-methyl-4-oxocyclohex-2-enecarboxylate (20653-52-5) → ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-methylenecyclohexancarboxylate (139932-51-7,139932-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CuI, BF₃*Et₂O, 2.) BF₃*Et₂O / 1.) Et₂O, -50 deg C, 5 min, 2.) Et₂O, -30 deg C, 1 h

2: 95 percent / sodium t-pentoxide / toluene / 2 h / Heating

With copper(l) iodide; boron trifluoride diethyl etherate; sodium tert-pentoxide; In toluene;

DOI:10.1080/00397919208019254

upstream raw materials:

methyl-triphenylphosphonium iodide

ethyl 3-(β-phenylethyl)-2,2-dimethyl-4-oxocyclohexancarboxylate

Ethyl 3-[2-(2-bromophenyl)ethyl]-2,2-dimethyl-4-methylenecyclohexanecarboxylate

4-carbethoxy-3-methyl-2-cyclohexen-1-one

Downstream raw materials:

1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2β-ol

(+/-)-podocarpa-8,11,13-triene-3α-ol

(+/-)-podocarpa-8,11,13-trien-3-one