Peracetic Acid → Acetyl 2-chlorobutyryl peroxide

HRID 437930Notes

Reaction equation

HRID 437930 reaction equation
[C:1]([O:4][OH:5])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Cl:12][CH:13]([CH2:17][CH3:18])[C:14](Cl)=[O:15]>O.CCOCC.C(Cl)(Cl)Cl>[Cl:12][CH:13]([CH2:17][CH3:18])[C:14]([O:5][O:4][C:1](=[O:3])[CH3:2])=[O:15]

Participants

7

Reactant 3

HCID 6585Peracetic AcidHCID 10340Sodium CarbonateHCID 1390532-Chlorobutanoyl chloride

Product 1

HCID 20372743Acetyl 2-chlorobutyryl peroxideYield 49.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-3 °C

Procedure

To 9.5 g. (0.05 moles) of 40% peracetic acid in 20 cc. H2O was added 3.2 g. (0.03 moles) of anhydrous sodium carbonate. The mixture was chilled to -3° C. with stirring and 7.1 g. (0.05 moles) of 2-chlorobutyryl chloride in 30 cc. chloroform added over a period of 8 minutes. After a total of 40 minutes at -3° to -6° C., ether and water were added. The organic phase was separated, washed once with cold 1% KOH solution, once with ice water, and once with cold saturated salt water. The concentrated material weighed 8.2 g., including 2.0 g. of dimethyl phthlate. Product A.O. analysis: theory, 8.14 found, 4.81; 59.1% pure; 49.5% yield.

Workup

  1. customThe organic phase was separated
  2. washwashed once with cold 1% KOH solution, once with ice water

Sources & evidence

ORD record
ord-224c55bc94ff4fc08d6eb74611a7f728
Source dataset
uspto-grants-1977_06
Patent number
US04032605

Reaction notes

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