Methanol → Methyl 4-tert-butyl-2-hydroxybenzoate

Temperature

0 °C

A dry reaction flask equipped with a stirring bar and a rubber septum was charged with 4-tert-butyl-2-(methoxymethoxy)benzoic acid (11.9 g, 50 mmol) and MeOH (166 mL). The solution was cooled to 0° C. and dry HCl gas was bubbled into the reaction. The reaction color changed from faint yellow to peach and again back to faint yellow. The reaction mixture was refluxed for 18 h, cooled to room temperature, and the solvent was removed. The resulting thick oil was diluted with CH2Cl2 (100 mL) and washed with H2O (100 mL) and 5% aqueous NaHCO3 solution (2×50 mL). The organic solution was dried (Na2 SO4) and the solvent was removed to obtain the requisite compound (9.10 g, 87%) as a colorless liquid, TLC Rf: 0.77 (10% EtOAc/n-hexanes).

1. customA dry reaction flask
2. customequipped with a stirring bar
3. customdry HCl gas was bubbled into the reaction
4. temperatureThe reaction mixture was refluxed for 18 h
5. temperaturecooled to room temperature
6. customthe solvent was removed
7. additionThe resulting thick oil was diluted with CH2Cl2 (100 mL)
8. washwashed with H2O (100 mL) and 5% aqueous NaHCO3 solution (2×50 mL)
9. customThe organic solution was dried (Na2 SO4)
10. customthe solvent was removed

ORD record

ord-175abd4a3920429783f80db0cbe00f49

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700628B2