Acetone → HCID 17861229, compound

HRID 1294119Notes

Reaction equation

HRID 1294119 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[OH:23][C:24]1[CH:37]=[C:36]([OH:38])[CH:35]=[CH:34][C:25]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[C:26]([C:25]1[CH:34]=[CH:35][C:36]([O:38][CH2:2][C:3]2[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12][C:13]=3[CH3:14])=[CH:5][CH:4]=2)=[CH:37][C:24]=1[OH:23])(=[O:27])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 17861229HCID 17861229, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole-(2.76 g), 2,4-dihydroxybenzophenone (2.00 g), anhydrous potassium carbonate (1.29 g) and acetone (50 mL) was heated under reflux for 0.15 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give crystals (1.72 g, 40%) of 4-[4-(4-benzoyl-3-hydroxyphenoxymethyl)phenoxymethyl]-5-methyl-2-phenyloxazole. Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 160-161° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.15 hrs
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-156568e1916e44f2addf5a31f2e2d489
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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