Reaction #1256713

Reaction equation

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

water

→

title compound

Yield 90.2%

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

Yield 90.2%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionextracted with chloroform (100 mL)
2. 2
   OtherThe organic layer was separated
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude product was purified by flash chromatography on silica gel eluting with hexane

Procedure

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.

Source