Epichlorohydrin → 2-[(4-Benzoylphenoxy)methyl]oxirane

HRID 1824666

Reaction equation

HRID 1824666 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)[CH:18]1[O:20][CH2:19]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 3528162-[(4-Benzoylphenoxy)methyl]oxirane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

As illustrated in FIG. 6, 100 mL of dried acetone were added to a dry, 250-mL round bottom flask, equipped with a magnetic stirrer, along with 15.05 grams of 4-hydroxybenzophenone, 32.1 grams of epichlorohydrin, and 6.2 grams of potassium carbonate. The solution was heated to reflux for 6 hours and then cooled to room temperature. The precipitated potassium chloride was filtered off, and the solution was evaporated to remove excess epichlorohydrin. The crude product was recrystallized from methanol. 1H NMR data confirmed the formation of the desired product.

Workup

  1. additionwere added to a dry, 250-mL round bottom flask
  2. temperatureThe solution was heated
  3. temperatureto reflux for 6 hours
  4. filtrationThe precipitated potassium chloride was filtered off
  5. customthe solution was evaporated
  6. customto remove excess epichlorohydrin
  7. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-11abb5634ed142ee9bd12b16b8fc0da6
Source dataset
uspto-grants-2006_05
Patent number
US07045366B2

Linked notes

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