4-Chlorobenzaldehyde → 5-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one

HRID 486054

反応式

HRID 486054 の反応式
[OH-].[Na+].[CH3:3][C:4]1([CH3:10])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>C(O)C>[CH3:3][C:4]1([CH3:10])[CH2:8][CH2:7][C:6](=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=2)[C:5]1=[O:9]

参加物

5

反応物 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 1382862,2-Dimethylcyclopentanone

生成物 1

HCID 534210215-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one収率 59.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

10% aqueous sodium hydroxide solution (100 ml) is added to a mixture of 2,2-dimethylcyclopentanone (10 g) and 4-chlorobenzaldehyde (13.8 g) in ethanol (100 ml) at 0° C. After 30 minutes, a thick slurry is filtered and the solid is washed and then dried. 2,2-Dimethyl-5-(4-chlorobenzylidene)-1-cyclopentanone (12.5 g), m.p. 120° C., is obtained. This compound, dissolved in THF (50 ml), is added to a solution formed in the following manner: sodium hydride (s0% dispersion in mineral oil) (1.9 g) in anhydrous DMSO (50 ml) is heated to 80° C. until the solid has dissolved completely. The solution is then diluted with THF (100 ml) and then cooled to -10° C. A solution of trimethylsulphonium iodide (11.5 g) in dimethyl sulphoxide (80 ml) is added to the mixture in the course of 10 minutes and the mixture is stirred for 15 minutes at -10° C. A solution of 2,2-dimethyl-4-chloro-5-(4-chlorobenzylidene)-1-cyclopentanone (11.8 g) in THF (100 ml) is then added.

後処理

  1. filtrationa thick slurry is filtered
  2. washthe solid is washed
  3. customdried

出典と根拠

ORDレコード
ord-b1de4ff2d4304c4b8b0fe3c45af4015d
出典データセット
uspto-grants-1994_03
特許番号
US05290791

関連ノート

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