Phenol → HCID 19759989, compound

HRID 1613853Notes

Reaction equation

HRID 1613853 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][C:21]([O:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidone2×HCID 21176463HCID 21176463, compound

Product 1

HCID 19759989HCID 19759989, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing one gram (3.2 mmoles) of 4,5-diphenyl-2-(p-fluorophenyl)-1,3-oxazole, 1.2 g (12 mmoles) of phenol, 2 g (14.5 mmoles) of anhydrous potassium carbonate and 10 ml of N-methylpyrrolidone (hereinafter NMP) is stirred and refluxed under nitrogen atmosphere for 40 minutes when gas chromatograph analysis indicates the disappearance of the starting material and the formation of a new compound. The reaction mixture is cooled, diluted with 30 ml of water, and stirred for 30 minutes. The colorless precipitate is filtered and recrystallized from 95 percent ethanol. The title compound (1.22 g, 99 percent yield) is recovered. The product has a melting point of 125° C.-126° C.

Workup

  1. temperaturerefluxed under nitrogen atmosphere for 40 minutes when gas chromatograph analysis
  2. temperatureThe reaction mixture is cooled
  3. stirringstirred for 30 minutes
  4. filtrationThe colorless precipitate is filtered
  5. customrecrystallized from 95 percent ethanol

Sources & evidence

ORD record
ord-62713c3cc1bb450284540fb847c932ac
Source dataset
uspto-grants-1993_03
Patent number
US05194562

Reaction notes

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