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

HRID 917955Notes

Reaction equation

HRID 917955 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4080ad020c2844d3aae0d54dfe32d5fc
Source dataset
uspto-grants-1976_07
Patent number
US03968216

Reaction notes

Loading…