Benzophenone → 2-Propenoic acid, 4-benzoylphenyl ester

HRID 1680892Notes

Reaction equation

HRID 1680892 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.[OH-].[Na+].[C:18](C1C=CC=CC=1)(=[O:25])[C:19]1C=CC=C[CH:20]=1.C(Cl)(=O)C=C>O>[C:18]([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)(=[O:25])[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 3102BenzophenoneHCID 13140Acryloyl chlorideHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 30151312-Propenoic acid, 4-benzoylphenyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 g quantity of 4-hydroxybenzophenone was added to 500 ml of water containing 22.0 g of sodium hydroxide. The solution was stirred until all of the benzophenone had dissolved. After the solution had cooled to 5°-10° C., there was added 45.5 g of acrylyl chloride over a period of 30 minutes, to yield a white solid which was recovered by filtration after the solution had been stirred for 2 hours at 5°-10° C. and an additional hour at room temperature. The white solid was recrystallized from ethanol and found to have m.p. 44°-46° C. Infrared and NMR spectra confirmed the structure of 4-acryloxybenzophenone.

Workup

  1. dissolutionhad dissolved
  2. temperatureAfter the solution had cooled to 5°-10° C.
  3. customto yield a white solid which
  4. filtrationwas recovered by filtration after the solution
  5. customThe white solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-442d3232c621408ba8f3a93e2a0f88bd
Source dataset
uspto-grants-1981_06
Patent number
US04276366

Reaction notes

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