تفاعل #2045015

ord-b1893d7b580a49718678470051e47742

معادلة التفاعل

Nc1ccc(O)cc1
4-aminophenol
O=C([O-])O.[Na+]
sodium bicarbonate
O=C(Cl)COCc1ccccc1
benzyloxy acetyl chloride
O=C(COCc1ccccc1)Nc1ccc(O)cc1
26
المردود 48.9%
O=C(COCc1ccccc1)Nc1ccc(O)cc1
2-Benzyloxy-N-(4-hydroxy-phenyl)-acetamide
المردود 48.9%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe solids were filtered off
  2. 2
    workup.ADDITIONcold water (500 ml) was added
  3. 3
    استخلاصCrude 26 was extracted into chloroform
  4. 4
    غسيلwashed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml)
  5. 5
    تجفيفdried over sodium sulphate
  6. 6
    workup.DISTILLATIONdistilled
  7. 7
    أخرىThe crude 26 was purified by column chromatography on silica gel

الإجراء التجريبي

To mixture of 4-aminophenol (20 g, 183.2 mmol) and sodium bicarbonate (17 grams, 202 mmol) in acetone (150 ml) at 0° C. was added benzyloxy acetyl chloride (40 g, 216.8 mmol) drop wise, followed by stirring at room temperature for 20 hours. The solids were filtered off, and cold water (500 ml) was added. Crude 26 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml), dried over sodium sulphate and distilled. The crude 26 was purified by column chromatography on silica gel using chloroform as eluant to get pure 26 (23 g, 48.9%) as a light orange syrup.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08409559B2uspto-grants-2013_04