Mesitylene → 2-Acetyl-6-methoxynaphthalene

HRID 1030843Notes

Reaction equation

HRID 1030843 reaction equation
C1(C)C=C(C)C=C(C)C=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:28][CH3:29])[C:23]=2Br)[CH:18]=1)(=[O:16])[CH3:15].BrC1C2C(=CC=CC=2)C=CC=1OC>>[C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:28][CH3:29])[CH:23]=2)[CH:18]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 7947MesityleneHCID 728601-Bromo-2-methoxynaphthaleneHCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 775062-Acetyl-6-methoxynaphthalene

Conditions

Temperature
0 °C

Procedure

51 Ml of mesitylene 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 3 hours under stirring at 0° C. and then it is worked as in example 1 obtaining 43.2 g of product with a yield equal to 88.2% 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-86812214cd644626a512c47d35e41acc
Source dataset
uspto-grants-1992_04
Patent number
US05107013

Reaction notes

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