Synthesis
The general procedure for the synthesis of p-phenylthiobenzyl alcohol from 4-phenylthiobenzaldehyde: 4-phenylthiobenzaldehyde and methanol were added to a reaction flask, and sodium borohydride was added in batches under stirring conditions, and the reaction mixture was naturally warmed up to 55 °C due to exotherm. The reaction was monitored by thin-layer chromatography (Expanding Agent: hexane/ethyl acetate=10:1) and took about 1 hour to complete. At the end of the reaction, the pH was adjusted to 6 by dropwise addition of hydrochloric acid and the reaction mixture was filtered. The filtrate was concentrated to dryness under reduced pressure (pressure 1330 Pa, temperature 45 °C) and methanol was recovered to give a viscous residue. To the residue was added an appropriate amount of dichloromethane, and the resulting mixture was washed with water until neutral and then dried with anhydrous sodium sulfate. The dried mixture was filtered and the filtrate was concentrated under reduced pressure (pressure 1720 Pa, temperature 25°C) to recover methylene chloride. After the concentrate was cooled to room temperature, a light yellow solid product was precipitated.
References
[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5217 - 5225
[2] Patent: CN107652238, 2018, A. Location in patent: Paragraph 0022; 0023
[3] Patent: CN107573288, 2018, A. Location in patent: Paragraph 0015; 0023
[4] Chemical Communications, 2009, # 7, p. 827 - 829
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3708 - 3712
