2,4-Dihydroxybenzophenone → 4-(4-Benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole

HRID 2221526Notes

Reaction equation

HRID 2221526 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:23]([C:17]1[CH:18]=[CH:19][C:20]([O:22][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:6][C:7]=2[CH3:8])=[CH:21][C:16]=1[OH:15])(=[O:24])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 230766154-(4-Benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazoleYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenyl-1,3-oxazole (46.10 g), (2,4-dihydroxyphenyl)(phenyl)methanone (50.14 g), potassium carbonate (48.51 g) and acetone (700 mL) was heated under reflux for 20 hrs. The reaction mixture was concentrated, water was poured into the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-(4-benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole as colorless crystals (49.6 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was poured into the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c1506d67c01040fcb90379c1e449401e
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…