Acetic Anhydride → 3-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-ol

HRID 1816406Notes

Reaction equation

HRID 1816406 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[N:10][OH:11].C(OC(=O)C)(=O)C.CCN(CC)CC.O.[Cl-].[Na+].O>>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[O:11][N:10]=2)=[CH:2][CH:7]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23713072Sodium chloride dihydrateHCID 136342142(2,4-Dihydroxyphenyl)(4-hydroxyphenyl)methanone Oxime

Product 1

HCID 1355269583-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-olYield 44.7%

Procedure

A mixture of (2,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone oxime (0.46 g, 1.87 mmol), acetic anhydride (0.19 g, 1.87 mmol) and Et3N (0.25 g, 2.44 mmol) was stirred at room temperature for 24 h. The mixture was pored into water/brine and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05) gave an off-white solid (0.19 g, 42% yield, m.p. 192-194° C.); MS m/e 226 (M−H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05)

Sources & evidence

ORD record
ord-0012fe911cf944efb5f5fd1d1c66166c
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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