تفاعل #46734

ord-6c54fae39cb14701a9a8fe9b4c28e164

معادلة التفاعل

CCCCCCCCOc1ccc(C(N)=O)c(O)c1
2-hydroxy-4-octyloxy-benzamide
CCC[CH2][Sn](=[O])[CH2]CCC
dibutyltinoxide
CCCCCCCCOc1ccc(C#N)c(O)c1
product
المردود 14.4%
CCCCCCCCOc1ccc(C#N)c(O)c1
2-Hydroxy-4-octyloxy-benzonitrile
المردود 14.4%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction mixture was evaporated to dryness on SiO2
  2. 2
    أخرىpurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:4)

الإجراء التجريبي

A solution of 2-hydroxy-4-octyloxy-benzamide (5.21 g; 19.7 mmol) and dibutyltinoxide (3.65 g; 14.6 mmol) was refluxed in toluene (60 mL) for 12 days. The reaction mixture was evaporated to dryness on SiO2 and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:4) to yield 700 mg (14%) product as yellow crystals. Mp. 69-71° C. MS (Direct; Cl): 248 (MH+).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07741352B2uspto-grants-2010_06