Water → 1-Chloro-3-phenoxypropan-2-one

HRID 372070

Reaction equation

HRID 372070 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][CH2:15][CH:16]([OH:25])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CC(C)=O.[Cr]>[Cl:14][CH2:15][C:16]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:25]

Participants

6

Reactant 3

HCID 962WaterHCID 943001-Chloro-3-phenoxy-2-propanolHCID 131709961Jones' reagent

Product 1

HCID 116224561-Chloro-3-phenoxypropan-2-oneYield 49.7%

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

8N Jones reagent (100 ml.) was added dropwise to a stirred solution of 1-chloro-2-hydroxy-3-phenoxypropane (28.3 g.) in acetone (100 ml.) during 1 hour while maintaining the reaction temperature at 20° C. The mixture was then stirred for 4 hours, and then sufficient water was added to dissolve the precipitated chromium salts. The mixture was extracted three times with diethyl ether and the combined ethereal extracts were dried over sodium sulphate, concentrated under reduced pressure, dried again over sodium sulphate, and concentrated further and distilled, to give 1-chloro-3-phenoxyacetone (13.9 g.), b.p. 150°-155° C./20 mm.Hg.

Workup

  1. extractionThe mixture was extracted three times with diethyl ether
  2. dry with materialthe combined ethereal extracts were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. dry with materialdried again over sodium sulphate
  5. concentrationconcentrated further
  6. distillationdistilled

Sources & evidence

ORD record
ord-aebca0dd54214c77b0232d4af4effbc5
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Linked notes

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