Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester

Base Information

• Chemical Name: Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester
• CAS No.: 72948-78-8
• Molecular Formula: C11H18O3
• Molecular Weight: 198.25882
• Mol file: 72948-78-8.mol

Synonyms:Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester;Ethyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate

Chemical Property of Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester

Chemical Property:

• Melting Point: 56.5-57.5 °C
• Boiling Point: 274.7±40.0 °C(Predicted)
• PKA: 14.84±0.40(Predicted)
• PSA: 46.53000
• Density: 1.212±0.06 g/cm3(Predicted)
• LogP: 1.63480

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 4-Hydroxybicyclo[2.2.2]octane-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 4-Hydroxybicyclo[2.2.2]octane-1-carboxylate acts as a reagent in the synthesis of 4-substituted bicyclo[2.2.2]oct-1-yl P-nitrobenzenesulfonates.

Technology Process of Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester

There total 6 articles about Bicyclo[2.2.2]octane-1-carboxylic acid, 4-hydroxy-, ethyl ester 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: 98.0%

ethyl 4-hydroxyspiro[bicyclo[2.2.2]octane-2,2'-[1,3]dithiolane]-1-carboxylate (72948-77-7) → ethyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate (72948-78-8)

Guidance literature:

With Raney-Ni; In ethanol; Reflux;

DOI:10.1002/chem.201901208

Reference yield:

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate (72653-21-5) → ethyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate (72948-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium ethanolate / ethanol / 15 h / 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C

3: Raney-Ni / ethanol / Reflux

With boron trifluoride diethyl etherate; sodium ethanolate; In ethanol; dichloromethane;

DOI:10.1002/chem.201901208

Reference yield:

ethyl 4-hydroxy-2-oxobicyclo[2.2.2]octane-1-carboxylate (72948-76-6) → ethyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate (72948-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C

2: Raney-Ni / ethanol / Reflux

With boron trifluoride diethyl etherate; In ethanol; dichloromethane;

DOI:10.1002/chem.201901208

upstream raw materials:

ethyl 4-hydroxyspiro[bicyclo[2.2.2]octane-2,2'-[1,3]dithiolane]-1-carboxylate

ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate

ethyl 4-hydroxy-2-oxobicyclo[2.2.2]octane-1-carboxylate

ethyl acetoacetate

Downstream raw materials:

4-p-Nitrobenzolsulfonyloxy-bicyclo<2.2.2>octan-1-carbonsaeureaethylester

4-Aminomethyl-bicyclo<2.2.2>octan-1-ol

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