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

HRID 486054

반응식

HRID 486054 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b1de4ff2d4304c4b8b0fe3c45af4015d
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290791

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