3-(Chlorocarbonyl)-cyclopentanecarboxylic acid methyl ester

Base Information

• Chemical Name: 3-(Chlorocarbonyl)-cyclopentanecarboxylic acid methyl ester
• CAS No.: 85174-63-6
• Molecular Formula: C₈H₁₁ClO₃
• Molecular Weight: 190.627
• DSSTox Substance ID: DTXSID10424051
• Mol file: 85174-63-6.mol

Synonyms:3-(CHLOROCARBONYL)-CYCLOPENTANECARBOXYLIC ACID METHYL ESTER;85174-63-6;SCHEMBL12265850;DTXSID10424051;Cyclopentanecarboxylic acid, 3-(chloroformyl)-, methyl ester, cis-

Chemical Property of 3-(Chlorocarbonyl)-cyclopentanecarboxylic acid methyl ester

Chemical Property:

• PSA: 43.37000
• LogP: 1.34110
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 190.0396719
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(C1)C(=O)Cl

Technology Process of 3-(Chlorocarbonyl)-cyclopentanecarboxylic acid methyl ester

There total 4 articles about 3-(Chlorocarbonyl)-cyclopentanecarboxylic acid methyl 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:

(+/-)-(1S,3R)-3-(methoxycarbonyl)cyclopentanecarboxylic acid (84545-00-6,96382-85-3,96443-42-4,111138-52-4,111138-70-6,111139-10-7) → (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate (85174-63-6,116595-44-9,116940-83-1)

Guidance literature:

With thionyl chloride;

Reference yield:

cis-1,3-cyclopentanedicarboxylic acid (876-05-1,826-02-8) → (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate (85174-63-6,116595-44-9,116940-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / acetic anhydride / 0.5 h / Heating

2: 1.) r.t., 19 h; 2.) 2 deg C, 12 days

3: 26.2 g / thionyl chloride, pyridine, DMF / benzene / 2 h / Heating

With pyridine; thionyl chloride; N,N-dimethyl-formamide; In acetic anhydride; benzene;

DOI:10.1139/v88-009

Reference yield:

cis-1,3-cyclopentanedicarboxylic acid anhydride (6054-16-6) → (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate (85174-63-6,116595-44-9,116940-83-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) r.t., 19 h; 2.) 2 deg C, 12 days

2: 26.2 g / thionyl chloride, pyridine, DMF / benzene / 2 h / Heating

With pyridine; thionyl chloride; N,N-dimethyl-formamide; In benzene;

DOI:10.1139/v88-009

upstream raw materials:

(+/-)-(1S,3R)-3-(methoxycarbonyl)cyclopentanecarboxylic acid

(1R,3S)-dimethyl cyclopentane-1,3-dicarboxylate

cis-1,3-cyclopentanedicarboxylic acid anhydride

cis-1,3-cyclopentanedicarboxylic acid

Downstream raw materials:

Benzoic acid (1S,3R)-3-(4-chloro-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

Benzoic acid (1S,3R)-3-(4-chloro-5-methyl-2-oxo-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

(+/-)-2,3-dihydro-1--2-thioxo-4(1H)-pyrimidinone benzoate

(+/-)-1--2,4(1H,3H)-pyrimidinedione benzoate