Oxalyl chloride → Anthraquinone-2-carbonyl Chloride

HRID 2072657

Reaction equation

HRID 2072657 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=1)(O)=[O:2].C(Cl)(=O)C([Cl:23])=O>ClCCl>[Cl:23][C:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 670302-Anthraquinonecarboxylic acid

Product 1

HCID 15025286Anthraquinone-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Structure (I-C) was prepared as follows. 2-carboxyanthraquinone was reacted with oxalyl chloride in dichloromethane (catalyzed by dimethylformamide) to yield 2-chlorocarbonylanthraquinone, which was then reacted with 1-hexanol in tetrahydrofuran (in the presence of triethylamine) to yield 2-n-hexoxycarbonylanthraquinone, which was then treated in a manner similar to Preparation A to prepare the Structure (I-C) compound with a yield of 50%. Structure was confirmed by IR and NMR spectroscopy.

Workup

  1. customThe compound of Structure (I-C) was prepared

Sources & evidence

ORD record
ord-1aade12be2404a799099d9c145ff8cb2
Source dataset
uspto-grants-1990_04
Patent number
US04913996

Linked notes

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