Anisole → 2-Acetyl-6-methoxynaphthalene

HRID 1030846Notes

Reaction equation

HRID 1030846 reaction equation
C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:27][CH3:28])[C:22]=2Br)[CH:17]=1)(=[O:15])[CH3:14].BrC1C2C(=CC=CC=2)C=CC=1OC>>[C:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:27][CH3:28])[CH:22]=2)[CH:17]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 4

HCID 7519AnisoleHCID 728601-Bromo-2-methoxynaphthaleneHCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 775062-Acetyl-6-methoxynaphthalene

Procedure

80 Ml of anisole and 18 g of anhydrous aluminum chloride are added to the solution of 2-acetyl-5-bromo-6-methoxynaphthalene obtained as in example 1a), while keeping the temperature at -10° C. The reaction mixture is kept for 24 hours under stirring at room temperature and then it is worked as in example 1 obtaining 38.5 g of product with a yield equal to 78.5% calculated on the basis of the starting material 1-bromo-2-methoxynaphthalene.

Workup

  1. customobtained as in example 1a),
  2. customat -10° C

Sources & evidence

ORD record
ord-328ec34eb7744fff948f442a90fe81b6
Source dataset
uspto-grants-1992_04
Patent number
US05107013

Reaction notes

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