Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (9CI)

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (9CI)
• CAS No.: 344294-32-2
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17908
• Mol file: 344294-32-2.mol

Synonyms:Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (9CI);FORMYL-CYCLOPENTANECARBOXYLIC ACID METHYL ESTER;3-FORMYL-CYCLOPENTANECARBOXYLIC ACID METHYL ESTER

Chemical Property of Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (9CI)

Chemical Property:

• PSA: 43.37000
• LogP: 0.77460

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (9CI)

There total 5 articles about Cyclopentanecarboxylic acid, 3-formyl-, methyl ester (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: 36.7%

(+)-cis-(1R,3S)-3-hydroxymethyl-1-carbomethoxycyclopentane (58240-93-0,96443-44-6) → methyl 3-formylcyclopentane-1-carboxylate (344294-32-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/acs.jmedchem.1c00163

Reference yield: 31.0%

2-methoxybicyclo<2.2.1>hept-2-ene (17190-90-8) → methyl 3-formylcyclopentane-1-carboxylate (344294-32-2) + (1R,5S,7R,8S)-7-Methoxy-5-methyl-3,4,6-trioxa-tricyclo[6.2.1.02,7]undecane (87051-04-5,87172-10-9,87172-11-0) + (1R,5R,7R,8S)-7-Methoxy-5-methyl-3,4,6-trioxa-tricyclo[6.2.1.02,7]undecane (87051-04-5,87172-10-9,87172-11-0)

Guidance literature:

With oxygen; In various solvent(s); at -78 ℃; for 3h; Yields of byproduct given; Irradiation; rose bengal;

DOI:10.1016/S0040-4020(01)96578-0

Reference yield:

cyclopentane?1,3?dimethyl formate (2435-36-1) → methyl 3-formylcyclopentane-1-carboxylate (344294-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / methanol / 12 h / 25 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 12.5 h / -78 - 25 °C

3: Dess-Martin periodane / dichloromethane / 2 h / 25 °C

With dimethylsulfide borane complex; Dess-Martin periodane; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 3: |Dess-Martin Oxidation;

DOI:10.1021/acs.jmedchem.1c00163

upstream raw materials:

2-methoxybicyclo<2.2.1>hept-2-ene

norborn-2-ene

acetic anhydride

cyclopentane?1,3?dimethyl formate

Downstream raw materials:

((E)-3-Propenyl)-cyclopentanecarboxylic acid

phenyl<3-(1-propenyl)cyclopent-1-yl>methanone