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

A solution of 4-tert-butyl-2-(methoxymethoxy)benzoic acid (61.80 g, 259 mmol) and MeOH (865 mL) was cooled in an ice bath. Gaseous HCl was sparged through the cold fluid for 30 min to saturate it, and the solution was then heated to reflux. A Soxhlet extractor containing 3 Å molecular sieves was used to absorb the water produced in the reaction. After 16 h the heating mantle was removed, and the solution was allowed to cool to ambient temperature. The filtrate was concentrated to a thick semisolid which was taken up in 1:1 water/CH2Cl2 (800 mL). The aqueous layer was extracted once with CH2Cl2 (100 mL), and the combined organic layers were washed with water (250 mL) and 5% (w/w) NaHCO3 (200 mL). The organic layer was dried (MgSO4), filtered and concentrated to 49.54 g (92%) of yellow oil:

1. customGaseous HCl was sparged through the cold fluid for 30 min
2. concentrationto saturate it
3. temperaturethe solution was then heated to reflux
4. additionA Soxhlet extractor containing 3 Å molecular sieves
5. customto absorb the water
6. customproduced in the reaction
7. customAfter 16 h the heating mantle was removed
8. concentrationThe filtrate was concentrated to a thick semisolid which
9. extractionThe aqueous layer was extracted once with CH2Cl2 (100 mL)
10. washthe combined organic layers were washed with water (250 mL) and 5% (w/w) NaHCO3 (200 mL)
11. dry with materialThe organic layer was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated to 49.54 g (92%) of yellow oil

ORD record

ord-5725c0e56974409fad22d836a0ede21a

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511066B2