Benzyl 4-Hydroxybenzoate → HCID 22261396, compound

To a solution of benzyl 4-hydroxybenzoate (25.3 g, 111 mmol) in N,N-dimethylformamide (60 ml) was added potassium tert-butoxide (12.4 g, 111 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was evaporated under reduced pressure and 2-bromopyridine (24.5 g, 155 mmol), a copper powder (1.76 g, 27.7 mmol) and N,N-imethylformamide (80 ml) were added. The mixture was stirred at 120° C. for 8 hrs. The reaction solution was filtered with celite, and the filtrate was evaporated under reduced pressure. To the residue was added water (500 ml), and the mixture was extracted with ethyl acetate (500 ml). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1). Recrystallization from ethyl acetate-hexane gave the objective substance (25.5 g, 73%).

1. stirringThe mixture was stirred at 120° C. for 8 hrs
2. filtrationThe reaction solution was filtered with celite
3. customthe filtrate was evaporated under reduced pressure
4. additionTo the residue was added water (500 ml)
5. extractionthe mixture was extracted with ethyl acetate (500 ml)
6. washThe extract was washed successively with water and saturated brine
7. dry with materialdried (anhydrous magnesium sulfate)
8. customevaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)
10. customRecrystallization from ethyl acetate-hexane
11. customgave the objective substance (25.5 g, 73%)

ORD record

ord-7b824920d969412eaad66c3e3c286d1b

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2