Acetylene → 1-Chloro-6-phthalimidohex-1-en-3-one

HRID 917955

반응식

HRID 917955 반응식
[Cl-:1].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:21])[N:9]([CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14])[C:8](=[O:16])[C:7]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:6]12.[CH:22]#[CH:23]>ClC(Cl)C(Cl)Cl>[Cl:1][CH:22]=[CH:23][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][N:9]1[C:8](=[O:16])[C:7]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:6]2[C:5]1=[O:21]

참가 물질

5

반응물 3

HCID 6326AcetyleneHCID 5948864-(1,3-Dioxoisoindolin-2-yl)butanoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 537373061-Chloro-6-phthalimidohex-1-en-3-one

시약·촉매·용매 1

HCID 65911,1,2,2-Tetrachloroethane용매

실험 절차

Aluminum chloride (43 g) is added to a stirred solution of 4-phthalimidobutyryl chloride (36.2 g) in 1,1,2,2-tetrachloroethane (400 ml), previously saturated with acetylene. Acetylene is bubbled through the solution overnight, with stirring, and the reaction mixture is then decomposed by the addition of crushed ice (300 g). The organic layer is separated and the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml). The combined organic solution is dried over sodium sulphate and concentrated. The residual solid is recrystallized from hexane affording 1-chloro-6-phthalimidohex-1-en-3-one, m.p. 92°C.

후처리

  1. customAcetylene is bubbled through the solution overnight
  2. additionthe reaction mixture is then decomposed by the addition of crushed ice (300 g)
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml)
  5. dry with materialThe combined organic solution is dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residual solid is recrystallized from hexane

출처 및 근거

ORD 기록
ord-4080ad020c2844d3aae0d54dfe32d5fc
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968216

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