Chemical Properties
Light brown powder. Solubility of 50% in anhydrous methanol, 50% in 95% ethanol, 0.06% in water; 0.1–0.5% in gasoline, varying with chemical nature of gasoline.
Synthesis
General method: 4-Aminophenol (1.1 eq.) and benzaldehyde (1 eq.) were dissolved in CH2Cl2 or toluene, Hantzsch ester (1.2 eq.) and S-benzyl isothiourea chloride (0.1 eq.) were added. The reaction mixture was stirred for 12 hours at room temperature (using CH2Cl2 as solvent) or at 70 °C (using toluene as solvent). After completion of the reaction, the mixture was filtered to recover the catalyst and washed several times with CH2Cl2. The filtrate was evaporated and the residue was purified by fast chromatography to give pure p-benzylaminophenol.
References
[1] Tetrahedron Letters, 2011, vol. 52, # 39, p. 5004 - 5007
[2] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7292 - 7300
[3] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4554 - 4564
[4] Journal of Fluorine Chemistry, 2010, vol. 131, # 8, p. 879 - 882
[5] Journal of Chemical Research, 2009, # 11, p. 686 - 688
