Propionyl chloride → 2-Methoxynaphthalene

HRID 344821

Reaction equation

HRID 344821 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](C(=O)CC)[CH:7]=[CH:6]2.[Br:17][C:18]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22](C(=O)CC)=[CH:23]2.C(Cl)(=O)CC>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[Br:17][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 759131-(6-Methoxy-2-naphthalenyl)-1-propanoneHCID 14719981-(5-Bromo-6-methoxy-2-naphthyl)-1-propanone

Product 2

HCID 71192-MethoxynaphthaleneHCID 728601-Bromo-2-methoxynaphthalene

Procedure

Compared with the preparation of analogues of the compound II-A, ie 1-(6-methoxy-2-naphthyl)-1-propanone (II, X=H) and 1-(5-bromo-6-methoxy-2-naphthyl)-1-propanone (II, X=Br) by a Friedel-Crafts reaction between propionyl chloride and, respectively, 2-methoxy-naphthalene and 1-bromo-2-methoxy-naphthalene, the following advantages are obtained:

Workup

  1. customCompared with the preparation of analogues of the compound II-A

Sources & evidence

ORD record
ord-cea67d77e28d4f65a55a0bdda9b98b9c
Source dataset
uspto-grants-1991_10
Patent number
US05053533

Linked notes

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