Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate

Base Information

• Chemical Name: Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate
• CAS No.: 23062-53-5
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.235
• Mol file: 23062-53-5.mol

Synonyms:Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate;4-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Chemical Property of Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate

Chemical Property:

• Melting Point: 72-74 °C
• Boiling Point: 257.2±40.0 °C(Predicted)
• PKA: 14.80±0.40(Predicted)
• PSA: 46.53000
• Density: 1.252±0.06 g/cm3(Predicted)
• LogP: 1.24470
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

Methyl 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: Methyl 4-Hydroxybicyclo[2.2.2]octane-1-carboxylate has been used as a reactant for the synthesis of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides.

Technology Process of Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate

There total 24 articles about Methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate 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: 99.0%

4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid (1127-13-5) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 4-hydroxybicyclo<2.2.2>octane-1-carboxylate (23062-53-5)

Guidance literature:

In methanol; hexane; at 20 ℃; for 2h;

Reference yield: 94.0%

methyl 4-acetoxybicyclo<2.2.2>octane-1-carboxylate (81687-91-4) → methyl 4-hydroxybicyclo<2.2.2>octane-1-carboxylate (23062-53-5)

Guidance literature:

With sodium methylate; In methanol; for 2h; Heating;

DOI:10.1021/jo00136a028

Reference yield: 65.0%

bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (18720-35-9) → methyl 4-hydroxybicyclo<2.2.2>octane-1-carboxylate (23062-53-5)

Guidance literature:

With 2,4,6-trimethyl-pyridine; water; tert-butylammonium hexafluorophosphate(V); In acetone; at 20 ℃; for 3h; Electrolysis;

DOI:10.1038/s41586-019-1539-y

upstream raw materials:

diazomethane

4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid

methyl 4-acetoxybicyclo<2.2.2>octane-1-carboxylate

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

Downstream raw materials:

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

1,4-Difluor-bicyclo<2.2.2>octan

4-Fluoro-bicyclo[2.2.2]octane-1-carbonyl chloride

amino-4-fluorobicyclo[2.2.2]octane

Refernces

• 1、 -. "ISOXAZOLYL-CARBONYLOXY AZABICYCLO[3.2.1]OCTANYL COMPOUNDS AS FXR ACTIVATORS". . . Retrieved 2018/09/25.
• 2、 -. "PYRAZOLES AND METHODS OF MAKING AND USING THE SAME". Page 40-41. . Retrieved 2010/02/08.