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

HRID 840796Notes

Reaction equation

HRID 840796 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-:23].[K+].[K+]>CC(=O)CC>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:23][C:5]1[CH:6]=[CH:7][C:2]([C:1](=[O:8])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:4]=1)[CH3:21]

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

This ester-linked benzophenone was prepared according to the method of PCT Patent Appln. No. WO 93/16131 (Everaerts et al.). In a first step, an ethyl-(4-benzoyl-phenoxy)acetate (EPBA) precursor was prepared by refluxing a mixture of 100.0 grams (0.51 moles) 4-hydroxybenizoplhenonie, 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). 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 NoM.

Workup

  1. customwas prepared
  2. temperatureby refluxing
  3. additiona mixture of 100.0 grams (0.51 moles) 4-hydroxybenizoplhenonie
  4. filtrationThe carbonate was filtered off
  5. customthe MEK removed on a rotovapor
  6. customThe residue was crystallized from isopropyl alcohol
  7. customto yield a white, flaky product with a sharp melting point of 82° C

Sources & evidence

ORD record
ord-45601e9111fe4cbab0e320bd2a7e7661
Source dataset
uspto-grants-2002_04
Patent number
US06369123B1

Reaction notes

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