تفاعل #2045040

ord-d913c2582c114058a876fdb14f39c7e9

معادلة التفاعل

O=C(O)CCCCCOc1ccc([N+](=O)[O-])cc1
6-(4-nitrophenoxy)hexanoic acid
O=C(O)CCCCCOc1ccc([N+](=O)[O-])cc1
6-(4-Nitrophenoxy)-hexanoic acid
OCCO
ethylene glycol
Cl
HCl
O=C(CCCCCOc1ccc([N+](=O)[O-])cc1)OCCO
54
المردود 78.3%
O=C(CCCCCOc1ccc([N+](=O)[O-])cc1)OCCO
6-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl ester
المردود 78.3%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىfor one hr
  2. 2
    أخرىDuring HCl gas bubbling the temp
  3. 3
    أخرىrose to 60° C
  4. 4
    أخرىThe crude reaction mass
  5. 5
    workup.ADDITIONwas poured onto ice (1 Kg)
  6. 6
    استخلاصextracted into ethyl acetate
  7. 7
    غسيلwashed with water (2×250 ml)
  8. 8
    تجفيفdried over sodium sulphate
  9. 9
    workup.DISTILLATIONdistilled
  10. 10
    أخرىto get crude 54, which
  11. 11
    أخرىwas purified by column chromatography on silica gel

الإجراء التجريبي

To a mixture of 6-(4-nitrophenoxy)hexanoic acid 53 (50 g, 197.62 mmol) and ethylene glycol (200 ml) was passed dry HCl gas for one hr. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto ice (1 Kg), extracted into ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 54, which was purified by column chromatography on silica gel using benzene as eluant to get pure 54 (46 g, 78.3%) as a light yellow syrup.

المصدر

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