반응 #1256713

반응 방정식

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

water

→

title compound

수율 90.2%

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

수율 90.2%

용매

DMF

반응 조건

후처리

1. 1
   추출extracted with chloroform (100 mL)
2. 2
   기타The organic layer was separated
3. 3
   건조dried over anhydrous Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude product was purified by flash chromatography on silica gel eluting with hexane

실험 절차

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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