Water → HCID 20326573, compound

HRID 372748Notes

Reaction equation

HRID 372748 reaction equation
[O-2:1].[O-2:2].[O-2:3].[Cr+6:4].O.[Br:6][CH2:7][CH:8]([OH:18])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1.[S:19](=[O:23])(=[O:22])([OH:21])[OH:20]>C1(C)C=CC=CC=1.CC(C)=O>[CH3:12][C:11]([CH3:16])=[O:10].[OH:22][S:19]([OH:23])(=[O:21])=[O:20].[O:1]=[Cr:4](=[O:3])=[O:2].[Br:6][CH2:7][C:8](=[O:18])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 10219390chromium (VI) trioxideHCID 20333505HCID 20333505, compound

Product 2

HCID 20326573HCID 20326573, compoundHCID 131709961Jones' reagent

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent2×

Procedure

Jones' reagent was prepared by dissolving chromium trioxide (26.7 g.) in concentrated sulphuric acid (23 ml.) and making the solution up to 100 ml. total volume with water. This solution was added with stirring to a solution of 1-bromo-3-(3-chlorophenoxy)propan-2-ol (53.0 g.) in toluene (75 ml.) and acetone (50ml.) under an atmosphere of nitrogen, at such a rate as to keep the temperature between 0 and 5° C. When the addition was complete, the reaction mixture was allowed to warm to room temperature and was stirred at that temperature for 16 hours. Toluene (50 ml.) and water (50 ml.) were added to the mixture and the organic layer was separated and shaken with saturated sodium bicarbonate solution (50 ml.). The whole mixture was filtered through "Hyflo" (trade mark) kieselguhr, and the aqueous layer was separated and discarded. The organic layer was washed with water (50 ml.) and dried over magnesium sulphate, and the solvent was removed under reduced pressure at a temperature below 60° C., to give a residue of 1-bromo-3-(3-chlorophenoxy)propan-2-one; the n.m.r. spectrum in deuteriochloroform showed characteristic peaks at:

Workup

  1. additionThis solution was added
  2. customthe temperature between 0 and 5° C
  3. additionWhen the addition
  4. customthe organic layer was separated
  5. stirringshaken with saturated sodium bicarbonate solution (50 ml.)
  6. filtrationThe whole mixture was filtered through "Hyflo" (trade mark) kieselguhr
  7. customthe aqueous layer was separated
  8. washThe organic layer was washed with water (50 ml.)
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent was removed under reduced pressure at a temperature below 60° C.

Sources & evidence

ORD record
ord-3ec63341d9d94bbb9633b096c9cc63f8
Source dataset
uspto-grants-1978_05
Patent number
US04092323

Reaction notes

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