Tert-Butylbenzene → 2-Acetyl-6-methoxynaphthalene

HRID 1030844Notes

Reaction equation

HRID 1030844 reaction equation
C(C1C=CC=CC=1)(C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[C:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:29][CH3:30])[C:24]=2Br)[CH:19]=1)(=[O:17])[CH3:16].BrC1C2C(=CC=CC=2)C=CC=1OC>>[C:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:29][CH3:30])[CH:24]=2)[CH:19]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 4

HCID 7366Tert-ButylbenzeneHCID 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

57 Ml of tert-butylbenzene and 8.2 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 16 hours under stirring at room temperature and then it is worked as in example 1 obtaining 41.8 g of product with a yield equal to 85.3% 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-56cd67c935334e7c86623b4167405eb6
Source dataset
uspto-grants-1992_04
Patent number
US05107013

Reaction notes

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