Water → 1-Chloro-3-phenoxypropan-2-one
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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
8 N 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
- extractionThe mixture was extracted three times with diethyl ether
- dry with materialthe combined ethereal extracts were dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- dry with materialdried again over sodium sulphate
- concentrationconcentrated further
- distillationdistilled
Sources & evidence
- ORD record
- ord-43186d6d408d444eab843eaecc02d028
- Source dataset
- uspto-grants-1982_04
- Patent number
- US04325967
Reaction notes
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