Epichlorohydrin → 4-Glycidyloxyphenyl benzyl ketone
Reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH2:6]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>>[CH2:6]([C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:1][CH:3]2[O:5][CH2:4]2)=[CH:19][CH:20]=1)=[O:14])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
Procedure
A 100 ml 3-neck round-bottom flask equipped with a magnetic stir bar, thermometer and reflux condenser was charged with 11.0 g epichlorohydrin, 5.0 g 4-hydroxyphenyl benzyl ketone, and 0.1 ml H20. The reactants were stirred on a hotplate. NaOH was then added, ~0.2 g per addition, up to a total of 0.95 g NaOH. The rate of NaOH addition was controlled to keep the reaction temperature below 100° C. At the end of the exothermic reaction, excess epichlorohydrin was removed by vacuum distillation with the flask temperature kept below 150° C. The residue was air-dried, then recrystallized twice from ethanol and redried. The yield was 2.8 g (44%), m.p. 81.0°-82.4° C. A 1H-NMR spectrum of this compound, with peak assignments, is provided in FIG. 1.
Workup
- customA 100 ml 3-neck round-bottom flask equipped with a magnetic stir bar
- temperaturethermometer and reflux condenser
- addition~0.2 g per addition
- customthe reaction temperature below 100° C
- customwas removed by vacuum distillation with the flask temperature
- customkept below 150° C
- customThe residue was air-dried
- customrecrystallized twice from ethanol
- customredried
- customA 1H-NMR spectrum of this compound, with peak assignments, is provided in FIG. 1
Sources & evidence
- ORD record
- ord-34e6b93f730244f5bd568e60d66dc35d
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05405913
Reaction notes
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