تفاعل #170967

ord-8d8c1ad925fa435f8b7bbb7966f51d1b

معادلة التفاعل

COC(=O)C(C)Cl
methyl 2-chloropropionate
O=[N+]([O-])c1ccc(O)cc1
4-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
[I-].[Na+]
sodium iodide
COC(=O)C(C)Oc1ccc([N+](=O)[O-])cc1
14
المردود 31.0%
COC(=O)C(C)Oc1ccc([N+](=O)[O-])cc1
2-(4-Nitrophenoxy)-propionic acid methyl ester
المردود 31.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةrefluxed for 20 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (3 L) was added
  4. 4
    ترشيحCrude 14 was filtered
  5. 5
    أخرىdried
  6. 6
    أخرىrecrystallised from a mixture of ethyl acetate:hexane (1:5)

الإجراء التجريبي

To a mixture of 4-nitrophenol (200 grm, 1.439 mol), anhydrous K2CO3 (800 grm, 5.789 mol) and sodium iodide (10 g, 66.7 mmol) in anhydrous acetone (2.75 L) was added methyl 2-chloropropionate (264 g, 2.154 mol) and refluxed for 20 hours. Acetone was distilled off and water (3 L) was added. Crude 14 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 14 (100 g, 31%) as a white fluffy powder with a m.p between 83-84° C.

المصدر

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