2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI)

Base Information

• Chemical Name: 2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI)
• CAS No.: 179249-42-4
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.225
• Mol file: 179249-42-4.mol

Synonyms:2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI)

Chemical Property of 2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI)

There total 9 articles about 2,3-Dioxabicyclo[2.2.2]octane,5-(1-methylethyl)-,(1alpha,4alpha,5bta)-(9CI) 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:

6-isopropylcyclohex-3-en-1-ol → 5-isopropyl-2,3-dioxabicyclo[2.2.2]octane (179249-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / n-BuLi / diethyl ether; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h

2: 50 percent / 105 °C

3: 1.) O₂, tetraphenylporphyrin, 2.) potassium azodicarboxylate, HOAc / 1.) CH₂Cl₂, irradiation, -78 deg C, 5 h, 2.) CH₂Cl₂, -78 deg C, 30 min; room temperature, overnight

With n-butyllithium; oxygen; potassium diazodicarboxylate; 5,15,10,20-tetraphenylporphyrin; acetic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo9604292

Reference yield:

bicyclo[4.2.0]oct-3-en-7-one → 5-isopropyl-2,3-dioxabicyclo[2.2.2]octane (179249-42-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / 30percent H₂O₂ / acetic acid; H₂O / 24 h / 0 °C

2: 55 percent / 1,10-phenanthrolein, diisopropylamine, n-BuLi / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min, 3.) warm to room temperature, 2 h

3: 81 percent / DIBAL / toluene / 2 h / -78 °C

4: 91 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

5: 46 percent / acetone, Raney Ni / ethanol / 12 h / Heating

6: 62 percent / n-BuLi / diethyl ether; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h

7: 50 percent / 105 °C

8: 1.) O₂, tetraphenylporphyrin, 2.) potassium azodicarboxylate, HOAc / 1.) CH₂Cl₂, irradiation, -78 deg C, 5 h, 2.) CH₂Cl₂, -78 deg C, 30 min; room temperature, overnight

With n-butyllithium; 1,10-Phenanthroline; boron trifluoride diethyl etherate; dihydrogen peroxide; oxygen; potassium diazodicarboxylate; 5,15,10,20-tetraphenylporphyrin; nickel; diisobutylaluminium hydride; acetic acid; diisopropylamine; acetone; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid; toluene;

DOI:10.1021/jo9604292

Reference yield:

3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one (34905-87-8) → 5-isopropyl-2,3-dioxabicyclo[2.2.2]octane (179249-42-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 55 percent / 1,10-phenanthrolein, diisopropylamine, n-BuLi / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 30 min, 3.) warm to room temperature, 2 h

2: 81 percent / DIBAL / toluene / 2 h / -78 °C

3: 91 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

4: 46 percent / acetone, Raney Ni / ethanol / 12 h / Heating

5: 62 percent / n-BuLi / diethyl ether; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h

6: 50 percent / 105 °C

7: 1.) O₂, tetraphenylporphyrin, 2.) potassium azodicarboxylate, HOAc / 1.) CH₂Cl₂, irradiation, -78 deg C, 5 h, 2.) CH₂Cl₂, -78 deg C, 30 min; room temperature, overnight

With n-butyllithium; 1,10-Phenanthroline; boron trifluoride diethyl etherate; oxygen; potassium diazodicarboxylate; 5,15,10,20-tetraphenylporphyrin; nickel; diisobutylaluminium hydride; acetic acid; diisopropylamine; acetone; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1021/jo9604292

upstream raw materials:

5-(1-methylethyl)cyclohexa-1,3-diene

3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one

Refernces