Anisole → 4'-Methoxyacetophenone

HRID 565134

反応式

HRID 565134 の反応式
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].S([O-])([O-])(=O)=O.[Mg+2]>[N+](C)([O-])=O.CCOCC.[Sc]>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:9](=[O:11])[CH3:10])=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 7519AnisoleHCID 7918Acetic AnhydrideHCID 24083Sulfuric acid magnesium salt (1:1)

生成物 1

HCID 74764'-Methoxyacetophenone収率 97.2%

試薬・触媒・溶媒 3

HCID 23952Scandium触媒HCID 3283Diethyl Ether溶媒HCID 6375Nitromethane溶媒

反応条件

温度
21 °C

実験手順

The catalytic effect of the scandium salt of 5-trifluoromethanesulfonyl-1,3-dibutyl-2-sulfonyl-barbituric acid, obtained in Example 25, towards a Friedel-Crafts reaction of acylation was evaluated in the following manner. In 40 ml of anhydrous nitromethane, there is added 887 mg (0.7 moles) of the scandium salt of 5-trifluoromethylsulfonyl-1,3-dibutyl-2-sulfonyl-barbituric acid, and 1.08 g (10 mmoles) of anisole and 2.04 g (20 mmoles) of acetic anhydride. After stirring during 10 min at 21° C., the reaction mixture was diluted with 50 ml of ether and the reaction was inhibited with 100 ml of a saturated solution of sodium bicarbonate NaHCO3. After filtration on Celite, the solution was extracted with three fractions of 50 ml ether, then the collected ether phase was washed with a saturated solution of potassium chloride. After drying the ether phase with magnesium sulfate and evaporation, 1.46 g of p-methoxyacetophenone (95% yield) were recovered with a purity characterized by a proton RMN higher than 99%.

後処理

  1. filtrationAfter filtration on Celite
  2. extractionthe solution was extracted with three fractions of 50 ml ether
  3. washthe collected ether phase was washed with a saturated solution of potassium chloride
  4. dry with materialAfter drying the ether phase

出典と根拠

ORDレコード
ord-fa95fa811c2545e2a80299e9984faeaf
出典データセット
uspto-grants-2001_01
特許番号
US06171522B2

関連ノート

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