Sulfuric Acid → 2-Propanone, 1-(acetyloxy)-3-chloro-

HRID 2412454Notes

Reaction equation

HRID 2412454 reaction equation
[C:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][Cl:8])(=[O:3])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.C(O)(C)C>CC(C)=O>[C:1]([O:4][CH2:5][C:6](=[O:9])[CH2:7][Cl:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 980693-Chloro-2-hydroxypropyl acetateHCID 131709961Jones' reagent

Product 1

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-Yield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-acetoxy-3-chloro-2-propanol (15.3 g) in acetone (250 ml) is dropwise added Jones reagent (37.4 ml) containing chromic anhydride (10.39 g) and conc. sulfuric acid (10.18 ml) in 1 hour, and the resultant mixture is stirred at room temperature for 3 hours. The reaction mixture is mixed with isopropanol (10 ml) and the insoluble material is filtered off. The organic layer is concentrated in vacuum, and the residue is distilled to give 1-acetoxy-3-chloro-2-propanone (9 g) as an oil boiling at 102°-104° C./15 mm Hg. The yield is 60.0%.

Workup

  1. filtrationthe insoluble material is filtered off
  2. concentrationThe organic layer is concentrated in vacuum
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-adacc33553984157af7895203b8ced9f
Source dataset
uspto-grants-1985_01
Patent number
US04492794

Reaction notes

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