Methanol → Methyl 3-tert-butyl-4-hydroxybenzoate

Temperature

70 °C

Methyl 4-hydroxybenzoate (3.00 g) was dissolved in methanesulfonic acid (15 mL), and 2-bromo-2-methylpropane (11.1 mL) was added to the solution, and then the mixture was stirred at 70° C. for 16 hours. To the reaction solution, methanol (20 mL) was added, and then the reaction mixture was stirred at 50° C. for 3 hours. 1N potassium hydroxide was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% potassium carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (1.83 g) as a pale yellow crystal.

1. stirringthe reaction mixture was stirred at 50° C. for 3 hours
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with an aqueous 10% potassium carbonate solution and saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

ORD record

ord-3291b6e597b141ebab37903d450adbc4

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367843B2