Hydrochloric Acid → 4-(Oxazol-2-yl)phenol

HRID 1046309Notes

Reaction equation

HRID 1046309 reaction equation
CS([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[CH:15][N:16]=2)=[CH:8][CH:7]=1)(=O)=O.[OH-].[K+].Cl>C1COCC1>[O:13]1[CH:14]=[CH:15][N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 109226274-(Oxazol-2-yl)phenyl methanesulfonate

Product 1

HCID 1356214594-(Oxazol-2-yl)phenolYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(oxazol-2-yl)phenyl methanesulfonate (11.2 g, 46.81 mmol) in THF (200 mL), a freshly prepared aqueous solution of KOH (40 wt. %, 13.2 mL, 93.6 mmol, 2 equiv.) was added. The reaction mixture was stirred at 80° C. for 4 hours and at ambient temperature overnight. Another 2 equiv. of aqueous solution of KOH (40 wt. %, 13.2 mL, 93.6 mmol) was then added and the reaction mixture was continuously stirred at 80° C. for 3 hours. After cooling, the reaction mixture was cautiously brought to pH 5 with 1 M aqueous HCl. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flashmaster chromatography on 50 g of silica gel using a gradient of 100% CH2Cl2→90% CH2Cl2+10% methanol gave 4.25 g (56% th.; 38% pract.) of 4-(oxazol-2-yl)phenol; 1H NMR (CD3OD) δ 7.86 (d, 1H), 7.84 (d, 2H), 7.20 (d, 1H), 6.88 (d, 2H) ppm.

Workup

  1. stirringthe reaction mixture was continuously stirred at 80° C. for 3 hours
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ca141ceca9f482389c30da46e51a893
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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