4-Chlorobutyryl chloride → HCID 20541536, compound

HRID 1065171Notes

Reaction equation

HRID 1065171 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:8][Si:9]([C:12]#[C:13][Si](C)(C)C)([CH3:11])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:8][Si:9]([CH3:11])([CH3:10])[C:12]#[C:13][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 84564Bis(trimethylsilyl)acetyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20541536HCID 20541536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 16.8 grams of 4-chlorobutyryl chloride and 20.4 grams of bis-trimethylsilylacetylene in 300 ml of dry methylene chloride, cooled in an ice bath, is added powdered anhydrous aluminum chloride, portionwise, over a period of 20 minutes. The mixture is stirred for 5 minutes, then the cooling bath is removed and the mixture stirred at room temperature for 4 hours. The mixture is poured into 500 ml of ice-water. The organic layer is separated, washed with water and brine, dried over anhydrous sodium sulfate and filtered through diatomaceous earth. The mother liquor is evaporated to dryness giving a brownish residue. The residue is Kugelrohr-distilled to give a colorless liquid.

Workup

  1. additionis added
  2. customthe cooling bath is removed
  3. stirringthe mixture stirred at room temperature for 4 hours
  4. additionThe mixture is poured into 500 ml of ice-water
  5. customThe organic layer is separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered through diatomaceous earth
  9. customThe mother liquor is evaporated to dryness
  10. customgiving a brownish residue
  11. distillationThe residue is Kugelrohr-distilled
  12. customto give a colorless liquid

Sources & evidence

ORD record
ord-6aa78150866d46e1841ae378d60ae868
Source dataset
uspto-grants-1982_05
Patent number
US04328359

Reaction notes

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