4-Hydroxybenzoic Acid → tert-Butyl 4-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-benzoic acid (3 g, 21.7 mmol) was stirred in toluene (35 ml, dried over mol. sieves). The solution was heated to 80° C. under N2, and N,N′-dimethylformamide di-tert-butyl acetal (10.42 mL, 43.4 mmol) was added over ca. 5 min. The mixture was stirred at 80° C. for 1 h 10 min., and cooled to rt. The solution was washed with water, twice with sat. NaHCO3 and sat. NaCl (15 mL each), dried over MgSO4, and concentrated to yield a yellow oil (2.77 g). The product was purified by flash chromatography (380 g silica, eluant: 4:6 AcOEt/heptane (2 L) and 1:1 AcOEt/heptane 700 mL) to yield white crystals (2.07 g, 49% yield).

Provenance & Evidence