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ChemicalBook CAS DataBase List 5-Methylbenzo[d]isoxazol-3(2H)-one
65685-49-6

5-Methylbenzo[d]isoxazol-3(2H)-one synthesis

3synthesis methods
61799-77-7 Synthesis
N,2-DIHYDROXY-5-METHYLBENZAMIDE

61799-77-7
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Yield:-

Reaction Conditions:

Stage #1: 2,N-dihydroxy-5-methylbenzamidewith 1,1'-carbonyldiimidazole in tetrahydrofuran; for 2 h;Reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;water; pH=1;

Steps:

4

The crude 2,N-dihydroxy-5-methyl-benzamide (3 g, 17.9 mmol) and carbonyl-diimidazole (5.8 g, 35.7 mmol) were refluxed in 500 mL THF for 2 hrs and then evaporated. Water was added to the residue and carefully acidified to pH 1 with 1N HCl. A solid precipitate formed which was filtered, washed with H2O and dried under high vacuum with heat (65-70° C.) to yield 2.1 g of 5-methyl-benzo[d]isoxazol-3-ol as a white solid.

References:

US2011/112158,2011,A1 Location in patent:Page/Page column 11