تفاعل #728467

ord-4c6f1f47224b4c09b3b659e71046e252

معادلة التفاعل

COC(=O)c1ccc(O)c([N+](=O)[O-])c1
4-hydroxy-3-nitro-benzoic acid methyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
BrCc1ccccc1
benzyl bromide
COC(=O)c1ccc(OCc2ccccc2)c([N+](=O)[O-])c1
4-Benzyloxy-3-nitro-benzoic acid methyl ester

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةat heated
  2. 2
    درجة الحرارةat reflux for 16 hours under a light argon flux
  3. 3
    أخرىwas evaporated
  4. 4
    أخرىthe two phases were separated
  5. 5
    استخلاصThe aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L)
  6. 6
    تجفيفThe combined organic phases were dried over sodium sulfate
  7. 7
    أخرىevaporated

الإجراء التجريبي

A solution of 4-hydroxy-3-nitro-benzoic acid methyl ester (30 g, 152 mmol) in acetone (1000 mL) was charged into a 2 L reactor and treated with K2CO3 (31.5 g, 228 mol) and benzyl bromide (52 g, 36.1 mL, 304 mmol). The mixture was mechanically stirred at heated at reflux for 16 hours under a light argon flux. After cooling to room temperature the solvent was evaporated. The residue was taken up in ethyl acetate/water and the two phases were separated. The aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L). The combined organic phases were dried over sodium sulfate and evaporated. 4-Benzyloxy-3-nitro-benzoic acid methyl ester thus obtained was used crude in the following reaction.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07696200B2uspto-grants-2010_04