HRID391487

反应详情

EQUATION

反应方程式

HRID 391487 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

3

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

A flask equipped with an overhead stirrer, thermometer and addition funnel was placed under a nitrogen atmosphere then charged with trans-2-hexenoic acid (69.8 g, 611 mmol), water (420 mL) and acetone (420 mL). Sodium bicarbonate (NaHCO3, 224 g, 2.66 mol) was then added portion-wise keeping the reaction temperature at 25±5° C. Once all of the sodium bicarbonate had been added, a solution of OXONE® (454 g, 738 mmol) in 4×10−4 M ethylenediaminetetraacetic acid disodium salt dehydrate (Na2EDTA; 1.32 L) was charged to the addition funnel and added over 90 minutes keeping the reaction temperature at 25±5° C. and the pH between 9.5 and 7.5. The reaction mixture was then allowed to stir for 16 h, after which time no (E)-hex-2-enoic acid was observed by HPLC analysis. The mixture was cooled to 0±5° C., acidified to pH 2 with 6 N HCl (515 mL, 2.8 mol) and extracted with ethyl acetate (EtOAc; 3×250 mL). The combined organic phases were dried over sodium sulfate (Na2SO4), filtered then concentrated under reduced pressure to provide the title compound (60.4 g, 76%) as a yellow oil.

WORKUP

后处理

  1. customA flask equipped with an overhead stirrer
  2. additionthermometer and addition funnel
  3. customat 25±5° C
  4. additionadded over 90 minutes
  5. customat 25±5° C.
  6. extractionextracted with ethyl acetate (EtOAc; 3×250 mL)
  7. dry with materialThe combined organic phases were dried over sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. concentrationthen concentrated under reduced pressure