Oxalyl chloride → 1-(4-Nitro-phenyl)-cyclopentanecarbonyl Chloride

HRID 1375078Notes

Reaction equation

HRID 1375078 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([Cl:21])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 28530781-(4-nitrophenyl)cyclopentane-1-carboxylic Acid

Product 1

HCID 210779351-(4-Nitro-phenyl)-cyclopentanecarbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 1-(4-nitro-phenyl)-cyclopentanecarboxylic acid (8.85 g) in dry dichloromethane (100 mL) was treated with oxalyl chloride (5.0 mL) and catalytic amount dry dimethylformamide (5 drops). The mixture was stirred at room temperature, under anhydrous conditions, for 16 hours then evaporated to give the title compound as an off white solid (100%), which was used without further purification.

Workup

  1. customthen evaporated

Sources & evidence

ORD record
ord-59134f0ebedf4cf0925243cae1dc276f
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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