hydroxylamine-O-sulfonic acid → 5-(P-Tolyl)isoxazole

HRID 1941329Notes

Reaction equation

HRID 1941329 reaction equation
NOS(O)(=O)=O.C[N:8](C)[CH:9]=[CH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:12].C(=O)(O)[O-].[Na+]>CO.O>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][N:8]=[CH:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 7300342-Propen-1-one, 3-(dimethylamino)-1-(4-methylphenyl)-

Product 1

HCID 2700155-(P-Tolyl)isoxazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

At 0° C. a solution of hydroxylamine-O-sulfonic acid (93 g) in dry methanol (700 ml) is added over 2 min to a solution of crude 3-dimethylamino-1-p-tolylprop-2-en-1-one (148 g) in dry methanol (1 l). The mixture is stirred at ambient temperature for 20 min, then carefully poured into a solution of sodium bicarbonate (150 g) in water (1 l). After standing at room temperature over night (for convenience) the precipitate is collected and dried to give crude 5-(4-methylphenyl)-isoxazole. In order to obtain purer product, the material can be purified by flash cromatography on silica gel, using hexane/ethyl acetate (4:1) as eluent.

Workup

  1. waitAfter standing at room temperature over night
  2. custom(for convenience) the precipitate is collected
  3. customdried

Sources & evidence

ORD record
ord-24bdf4ec42bc4072b18052420a9f16b0
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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