Benzophenone → Acetic acid, (4-benzoylphenoxy)-, ethyl ester

HRID 1654548Notes

Reaction equation

HRID 1654548 reaction equation
C(C1C=CC=CC=1)(=O)C.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[OH:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1.Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29](=[O:30])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:37][CH:38]=1)[CH3:45]

Participants

7

Reactant 5

HCID 3102BenzophenoneHCID 7410AcetophenoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 4686517Acetic acid, (4-benzoylphenoxy)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

This molecule is an important precursor for the synthesis of the multifunctional acetophenone and benzophenone crosslinking agents disclosed in this application. The ethyl-(4-benzoyl-phenoxy)acetate was prepared by refluxing a mixture of 100.0 grams (0.51 moles) 4-hydroxybenzophenone, 85.2 grams (0.51 moles) ethyl bromoacetate and 800 ml of 2-butanone (MEK) in the presence of an excess of potassium carbonate (209 grams or 1.5 moles). After three hours, the carbonate was filtered off and the MEK removed on a rotovapor. The residue was crystallized from isopropyl alcohol to yield a white, flaky product with a sharp melting point of 82° C. The structure was confirmed by NMR.

Workup

  1. temperatureby refluxing
  2. filtrationthe carbonate was filtered off
  3. customthe MEK removed on a rotovapor
  4. customThe residue was crystallized from isopropyl alcohol
  5. customto yield a white, flaky product with a sharp melting point of 82° C

Sources & evidence

ORD record
ord-4fc385aace7b45d4af3f3bd4be529699
Source dataset
uspto-grants-1995_04
Patent number
US05407971

Reaction notes

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