Uses
4-(Boc-amino)phenol, is used to protect amine in the solid phase synthesis of peptides, used to produce [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-carbamic acid tert-butyl ester at ambient temperature. This reaction will need reagent imidazole and solvent dimethylformamide, CH2Cl2.
Synthesis
General procedure for the synthesis of oxycarbonyloxy-4-hydroxyaniline from di-tert-butyl dicarbonate and 4-aminophenol: Di-tert-butyl dicarbonate (24.07 g, 110.3 mmol) was slowly added to a methanol (200 mL) solution containing 4-aminophenol (10.97 g, 100.5 mmol) and triethylamine (30 mL). The reaction mixture was stirred at room temperature (22°C) for 14 hours. After completion of the reaction, the solvent was removed by rotary evaporation. The residue was dissolved in ethyl acetate (250 mL) and extracted with 0.25N aqueous hydrochloric acid (100 mL). The organic phase was separated and washed sequentially with saturated aqueous ammonium chloride solution (3 x 50 mL) and dried over anhydrous sodium sulfate. Finally, the solvent was removed by rotary evaporation to give the white solid product oxocarbonyl-4-hydroxyaniline (20.91 g, 100% yield, ESI-MS (m/z) 208.1 [M-H]-).
References
[1] Patent: EP1609789, 2005, A1. Location in patent: Page/Page column 12
[2] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264
[3] Chemical Communications, 2013, vol. 49, # 51, p. 5757 - 5759
[4] Organic Letters, 2016, vol. 18, # 21, p. 5728 - 5731
[5] Comptes Rendus Chimie, 2013, vol. 16, # 11, p. 962 - 966
