Allyl bromide → 4-Allyloxybenzophenone

HRID 1372195Notes

Reaction equation

HRID 1372195 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.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24]>CC(=O)CC>[CH2:24]([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:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 2579104-Allyloxybenzophenone

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
65 °C

Procedure

4-hydroxybenzophenone (186.7 g, 940 mmol, Fluka Chemical) was dissolved in 2-butanone (700 mL, Fisher Scientific) in a 2L four-necked flask equipped with a mechanical stirrer, reflux condenser, addition funnel and internal temperature probe. K2CO3 (195 g, 1.41 mol, Aldrich Chemical) was added to the reactor, and the contents was placed under a slow N2 purge. Allyl bromide (123 mL, 1.41 mol, Aldrich Chemical) was charged to the addition funnel. The pot temperature was raised to 65° C., at which point the allyl bromide was added over the course of 30 minutes. The reaction was stirred for 6.5 h at 65° C. after the addition was completed. At this point no starting material was present as determined by GC analysis.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux
  3. additioncondenser, addition funnel
  4. custompurge
  5. additionwas added over the course of 30 minutes
  6. additionafter the addition

Sources & evidence

ORD record
ord-af6006837def41468fcf5b631aa60762
Source dataset
uspto-grants-2007_01
Patent number
US07157535B2

Reaction notes

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