mixture was poured on vacuum filter and the product cake was washed with water. After drying, there was obtained of
crystalline 3,5-di-
tert
-butyl-4-hydroxybenzaldehyde.
2.
Preparation of 2,6-di-
tert
-Butyl-4-vinylphenol by Wittig reaction
Methyltriphenylphosphonium iodide was prior prepared by adding methyl iodide
(6.23 mL g, 100 mmol) into a solution of triphenylphosphine ( 26.2 g, 100 mmol) in THF (100 ml). After there action
proceeded approximately for 3 hours, a white precipitate formed was filtered, wash with cold THF and dried in air to
give methyltriphenylphosphonium iodide as a fine white crystalline solid. Under an inert atmosphere, a solution of
methyltriphenylphosphonium iodide (12.9 g 36 mmol) in dry THF (50 mL) was cooled to 0°C. Potassiump
tert
p
butylate (1.6 M in THF, 22.5 mL, 36 mmol) was added dropwise with vigorous stirring for 30 mins. The 3,5-di-
tert
-
butyl-4-hydroxybenzaldehyde was added dropwise with vigorous stirring for 1 hour. Once the addition complete, the
reaction was allowed to warm to room temperature. Once all starting material was consumed the reaction was filtered
through a pad of silica and concentrated. The product was purified by column chromatography (eluting with 10%
diethyl ether in hexane, on silica).
3.
Product purification by column chromatography
Hexane was added into silica gel and stirred in beaker for about 5 mins. Hexane and silica gel in form of
slurry was then poured into a column. The product (2,6-DBVP) was added into column and eluted by the solution of
10% of diethyl ether in hexane. The 2,6-DBVP obtained was characterized by TLC.
4.
Characterization of 2,6-DBVP by FTIT spectroscopy
Structure of 2,6-DBVP was characterized by FTIR spectroscopy. Fourier transform infrared (FTIR) spectra
were obtained by means of Cooperation model Omnic. ESP Magna-IR 560 spectrometer, Nicolet.
