1-Naphthoic acid → 1-Naphthalenecarbonyl chloride

HRID 2231844Notes

Reaction equation

HRID 2231844 reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:17])=O>CN(C)C=O.C(Cl)Cl>[C:1]1([C:11]([Cl:17])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 68471-Naphthoic acidHCID 65578Oxalyl chloride

Product 1

HCID 701461-Naphthalenecarbonyl chlorideYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

a mixture of 17.2 g (0.1 mole) 1-naphthoic acid, 14 g (0.11 moles) oxalyl chloride, 150 ml methylene chloride and three drops DMF (dimethylformamide) were stirred for about 24 hours. The clear reaction mixture was stripped to give about 19.1 g of the 1-naphthoyl chloride as a brown liquid which was used in step (b) without further isolation.

Sources & evidence

ORD record
ord-9fe9bb9855324c47a2866a607ad2f820
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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