5-exo-Jod-6-endo-hydroxy-bicyclo[2.2.2]octan-2-carbonsaeure-γ-lacton

Base Information

• Chemical Name: 5-exo-Jod-6-endo-hydroxy-bicyclo[2.2.2]octan-2-carbonsaeure-γ-lacton
• CAS No.: 91739-70-7
• Molecular Formula: C₉H₁₁IO₂
• Molecular Weight: 278.09
• Mol file: 91739-70-7.mol

Synonyms:

Chemical Property of 5-exo-Jod-6-endo-hydroxy-bicyclo[2.2.2]octan-2-carbonsaeure-γ-lacton

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-exo-Jod-6-endo-hydroxy-bicyclo[2.2.2]octan-2-carbonsaeure-γ-lacton

There total 2 articles about 5-exo-Jod-6-endo-hydroxy-bicyclo[2.2.2]octan-2-carbonsaeure-γ-lacton 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:

Bicyclo<2.2.2>oct-5-ene-2-carboxylic acid (40610-12-6) → bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid (20507-56-6,20507-57-7,40335-74-8,40610-12-6,41977-03-1,41977-04-2) + endo-5-hydroxy-exo-6-iodo-endo-3-carboxybicyclo<2.2.2>octane-γ-lactone (40335-77-1,69778-99-0,91739-66-1,91739-70-7,91739-71-8,103000-84-6)

Guidance literature:

With sodium hydroxide; iodine; potassium iodide; In dichloromethane; water; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.44.296

Reference yield:

ethyl exo-bicyclo<2.2.2>oct-5-ene-2-carboxylate → bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid (20507-56-6,20507-57-7,40335-74-8,40610-12-6,41977-03-1,41977-04-2) + endo-5-hydroxy-exo-6-iodo-endo-3-carboxybicyclo<2.2.2>octane-γ-lactone (40335-77-1,69778-99-0,91739-66-1,91739-70-7,91739-71-8,103000-84-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; iodine; potassium iodide; Yield given. Multistep reaction. Yields of byproduct given; 1.) H₂O, MeOH, 60 deg C, 4 h.; 2.) H₂O, CH₂Cl₂;

DOI:10.1002/hlca.19840670723

Reference yield:

endo-5-hydroxy-exo-6-iodo-endo-3-carboxybicyclo<2.2.2>octane-γ-lactone (40335-77-1,69778-99-0,91739-66-1,91739-70-7,91739-71-8,103000-84-6) → 6-exo-methylbicyclo<2.2.2>oct-2-endo-yl p-toluenesulfonate

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / 12 h

2: TsOH / CH₂Cl₂ / 14 h / 20 °C

3: Et₃N, H₂ / 10percent Pd/C / methanol

4: 1.) MeOK; 2.) 2N NaOH / 1.) 18-crown-6 / 1.) benzene, MeOH, reflux, 45 min.; 2.) acetone, 12 h.

5: 93 percent / diethyl ether

6: 95 percent

7: 93 percent / LiAlH₄ / diethyl ether

8: pyridine

9: 91 percent / pyridinium p-toluenesulfonate / methanol

10: 87 percent / LiAlH₄ / tetrahydrofuran / 30 h / Heating

11: 93 percent / pyridine

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; potassium methanolate; hydrogen; pyridinium p-toluenesulfonate; triethylamine; palladium on activated charcoal; 18-crown-6 ether; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1002/hlca.19840670723

upstream raw materials:

Bicyclo<2.2.2>oct-5-ene-2-carboxylic acid

Downstream raw materials:

6-exo-hydroxybicyclo<2.2.2>octane-2-exo-carboxylic acid

6-endo-hydroxybicyclo<2.2.2>octane-2-exo-carboxylic acid