تفاعل #1256713

معادلة التفاعل

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

water

→

title compound

المردود 90.2%

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

المردود 90.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with chloroform (100 mL)
2. 2
   أخرىThe organic layer was separated
3. 3
   تجفيفdried over anhydrous Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe crude product was purified by flash chromatography on silica gel eluting with hexane

الإجراء التجريبي

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.

المصدر