Is this first reaction of general applicability? If so, then it is a new way to synthesize 2C-T-X precursors. The second reaction is a formylation I have never seen before...
Methyl (3,5-diisopropyl-4-hydroxy)benzenesulfonate (6).
To 2.90 g (16.2 mmol) of 2,6-diisopropylphenol (1) dimethyl sulfate (8 g, 63.4 mmol) was added dropwise maintaining the temperature at 20-30 C. The solution was refluxed under stirring for 1 h and, after cooling, was diluted with cold water. Stirring was continued overnight at room temperature, and then the organic phase was extracted with CHCl3 (20 mL) and dried (Na2SO4) and the solvent removed by rotary evaporation. The residue was purified by silica gel column chromatography [petroleum ether/ethyl acetate 8/2 (v/v) as eluent)] to give 2 g (45%yield) of 6: mp 68-70 C.
3,5-Diisopropyl-4-hydroxybenzaldehyde (7).
To a solution of 2,6-diisopropylphenol (1) (1.5 g, 8.4 mmol) in glacial acetic acid (80 mL) were added 40% formaldehyde (1.5 mL) and 30% NH4OH (1.12 mL). After 24 h on the steam bath, the solvent was evaporated under reduced pressure and the residue dissolved in CHCl3 (20 mL), washed with 5% NaHCO3, and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by silica gel column chromatography [petroleum ether/ethyl acetate 9/1 (v/v) as eluent)] to give 0.60 g (35%yield) of 7.
Ref: J. Med. Chem., 41 (11), 1846-1854 (1998)
