Sulfuric Acid → 1,4-Dibromo-2,2-diethoxy-3-butanone

HRID 1262648

반응식

HRID 1262648 반응식
[Br:1][CH2:2][C:3](=[O:8])[C:4](=[O:7])[CH2:5][Br:6].[CH2:9]([O:11]C(OCC)OCC)[CH3:10].S(=O)(=O)(O)O.[CH3:24][CH2:25]CCCC>C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]([O:11][CH2:9][CH3:10])([O:8][CH2:24][CH3:25])[C:4](=[O:7])[CH2:5][Br:6]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 227471,4-Dibromo-2,3-butanedioneHCID 31214Ethyl orthoformate

생성물 1

HCID 131009731,4-Dibromo-2,2-diethoxy-3-butanone수율 84%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 40 g (0.164 mol) of 1,4-dibromo-2,3-butanedione, 60 ml (0.36 M) of triethylorthoformate, and 2 ml of concentrated sulfuric acid was stirred at room temperature for 14 hours, then diluted with 600 ml of chloroform, and washed successively with 100 ml portions of water, 0.5 N hydrochloric acid and saturated sodium chloride solution. The organic solution was dried over anhydrous sodium sulfate filtered, and evaporated leaving an oil. The oil was taken up into 300 ml of hexane and filtered to remove some insoluble material. The hexane filtrate was cooled in a dry-ice/acetone bath, and the resulting precipitate was collected by filtration and dried to give 44 g (84%) of 1,4-dibromo-2,2-diethoxy-3-butanone as a white crystalline solid, mp 40°-41.5°; nmr (CDCl3) (δ): 4.50 (s, 2H); 3.6-3.2 (m, 6H); 1.22 (t, 6H).

후처리

  1. washwashed successively with 100 ml portions of water, 0.5 N hydrochloric acid and saturated sodium chloride solution
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customleaving an oil
  6. filtrationfiltered
  7. customto remove some insoluble material
  8. temperatureThe hexane filtrate was cooled in a dry-ice/acetone bath
  9. filtrationthe resulting precipitate was collected by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-bcf13641181c492697792f28e0a7439f
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04452987

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