Acetyl chloride → 2-Acetylnaphthalene

HRID 2071842Notes

Reaction equation

HRID 2071842 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[N+]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-])=O>>[C:1]([C:14]1[CH:15]=[CH:16][C:17]2[C:12](=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7416NitrobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 71222-Acetylnaphthalene

Procedure

The compounds of Formula I can be prepared from known starting compounds. For example, one such method by which they can be prepared involves the reaction of a substituted naphthalene with acetyl chloride in nitrobenzene in the presence of about three molar equivalents of aluminum chloride to afford the corresponding 2-acetylnaphthalene derivative. The resulting derivative is heated with morpholine in the presence of sulfur at 150° C.; the resulting product is refluxed with concentrated hydrochloric acid or alcoholic sodium hydroxide followed by acidification to furnish the corresponding 2'-naphthylacetic acid derivative.

Workup

  1. customThe compounds of Formula I can be prepared

Sources & evidence

ORD record
ord-ad080c820e6c49dc9c9365a484bb5b99
Source dataset
uspto-grants-1977_09
Patent number
US04048330

Reaction notes

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