反应 #1256713

反应方程式

3,5-di-tert-butyl-4-hydroxycinnamic acid

water

→

title compound

收率 90.2%

2,6-di-tert-butyl-4-vinyl-phenol

收率 90.2%

溶剂

DMF

反应条件

后处理

1. 1
   萃取extracted with chloroform (100 mL)
2. 2
   其他The organic layer was separated
3. 3
   干燥dried over anhydrous Na2SO4
4. 4
   过滤filtered
5. 5
   浓缩concentrated in vacuo
6. 6
   其他The crude product was purified by flash chromatography on silica gel eluting with hexane

实验过程

A solution of 3,5-di-tert-butyl-4-hydroxycinnamic acid (2.77 g, 10 mmol) in dry DMF (20 mL) was refluxed at 150° C. under N2 for 2 h with stirring. The resulting mixture was then poured into water (200 mL) and extracted with chloroform (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with hexane, to give 2.094 g (90.2%) of the title compound as a colorless solid: mp 51-51.5° C.; 1H NMR (400 MHz, CDCl3): δ 7.248 (s, 2H), 6.666 (d×d, 1H, J1=10.8 Hz, J2=17.6 Hz), 5.587 (d, 1H, J=16.8 Hz), 5.241 (s, 1H), 5.094 (d, 1H, J=10.8 Hz), 1.456 (s, 18H); 13C NMR (100 MHz, CDCl3): δ 153.980, 137.529, 136.055, 129.040, 123.216, 110.996, 34.565, 30.507; Anal. Calcd. for C16H24O: C, 82.70; H, 10.41. Found; C, 83.08; H, 10.37.

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