تفاعل #170993

ord-d17d530434914752a853376796162732

معادلة التفاعل

O=C(O)COc1ccc([N+](=O)[O-])cc1
(4-nitrophenoxy)acetic acid
O=C(O)COc1ccc([N+](=O)[O-])cc1
(4-Nitrophenoxy)acetic acid
CCN(CC)CC
triethyl-amine
COC(=O)CCl
methyl chloroacetate
COC(=O)COC(=O)COc1ccc([N+](=O)[O-])cc1
44
المردود 90.8%
COC(=O)COC(=O)COc1ccc([N+](=O)[O-])cc1
(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester
المردود 90.8%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةunder reflux for 8 hours
  2. 2
    ترشيحSolids were filtered off
  3. 3
    workup.ADDITIONpoured onto cold 5% sodium bicarbonate solution (4 L)
  4. 4
    ترشيحCrude 44 was filtered
  5. 5
    أخرىdried
  6. 6
    أخرىrecrystallised from chloroform:hexane (1:6)

الإجراء التجريبي

To a mixture of (4-nitrophenoxy)acetic acid 22 (150 g, 761.4 mmol) and triethyl-amine (85 g, 840 mmol) in acetone (750 ml) was added methyl chloroacetate (91.6 g, 844 mmol) drop wise and stirred under reflux for 8 hours. Solids were filtered off and poured onto cold 5% sodium bicarbonate solution (4 L). Crude 44 was filtered, dried and recrystallised from chloroform:hexane (1:6) to get pure 44 (186 g, 90.8%) as a white powder with an m.p. between 88-90° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08846845B2uspto-grants-2014_09