4-(4-Benzyloxyphenyl)oxazole → 4-(Oxazol-4-yl)phenol

HRID 1030459Notes

Reaction equation

HRID 1030459 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][O:18][CH:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]=[CH:17][O:18][CH:19]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 198202404-(4-Benzyloxyphenyl)oxazole

Product 1

HCID 124631404-(Oxazol-4-yl)phenolYield 45.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(4-Benzyloxyphenyl)oxazole (360mg) was dissolved in methanol (10 ml). 5% Palladium on carbon (containing 50% water) (300 mg) was added to the solution, and the mixture was subjected to catalytic reduction for 80 minutes. The catalyst was filtered off from the reaction mixture, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel [eluting solvent: ethyl acetate-hexane (1:2)] to give 4-(4-hydroxyphenyl)oxazole (105 mg, 45.5%). The product was further purified by recrystallization from diethyl ether-hexane. m.p. 147.5°-148° C.

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel [eluting solvent: ethyl acetate-hexane (1:2)]

Sources & evidence

ORD record
ord-3c3d6c85759140c3a5694ab18e3bc25e
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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