Dichloromethane → HCID 131719874, compound

HRID 974771Notes

Reaction equation

HRID 974771 reaction equation
[Cl:1][CH2:2][CH2:3]CC(Cl)=O.CC1[O:14][CH:13]([CH3:15])[O:12][CH:11]([CH3:16])O1.C(=O)(O)[O-].[Na+].[Cl:22]CCl>>[Cl:1][CH2:2][CH2:3][CH2:15][C:13]([O:12][CH:11]([CH3:16])[Cl:22])=[O:14]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 31264Paraldehyde2×HCID 783704-Chlorobutyryl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 131719874HCID 131719874, compoundYield 58.6%

Conditions

Temperature
85 °C

Procedure

4-Chlorobutyryl chloride (12.69 g, 90 mmol) was mixed with paraldehyde (3.964 g, 30 mmol) and heated at 85° C. for 90 minutes. Additional paraldehyde (1.35 g) was added and the reaction mixture was stirred at 85° C. for an additional hour. The reaction mixture as cooled to room temperature, diluted with dichloromethane (100 ml) and stirred with saturated aqueous sodium bicarbonate (50 ml) at room temperature for 10 minutes. The dichloromethane layer was separated, dried over sodium sulfate and concentrated in vacuo to yield Cl(CH2)3CO2CHClCH3 which was vacuum distilled (55°-58° C. at 0.1 mm, 9.65 g, 58.6% yield) whose structure was confirmed by NMR.

Workup

  1. temperatureThe reaction mixture as cooled to room temperature
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96a15f1545624fc9b793d023c56316ac
Source dataset
uspto-grants-1997_03
Patent number
US05607691

Reaction notes

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