Synthesis
The general procedure for the synthesis of 4-n-pentyloxybenzaldehyde from 1-bromopentane and p-hydroxybenzaldehyde is as follows: it was prepared by Williamson ether synthesis. This was done as follows: 4-hydroxybenzaldehyde (8.72 g, 71.5 mmol) was added to a solution of ethanol (60 mL) containing potassium hydroxide (4 g). Subsequently, n-alkyl halides (71.5 mmol) were added to the mixture (methyl iodide was used for the preparation of A1, while n-alkyl bromide was used for the preparation of A1-A13) and the reaction mixture was heated under reflux conditions. The reaction progress was monitored by thin layer chromatography (TLC) using chloroform as eluent to determine the optimal time for each reaction. After completion of the reaction, ethanol was removed by evaporation and the residue was dissolved in ether. The ether layer was washed sequentially with 10% aqueous potassium hydroxide and water until the pH of the wash solution reached 7. Finally, the organic layer was dried with anhydrous sodium sulfate, and evaporation afforded the target product, 4-n-pentyloxybenzaldehyde. The specific reaction conditions for each compound are detailed in Table 1.
References
[1] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 267 - 276
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 277 - 288
[3] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 151 - 154
[4] Molecular Crystals and Liquid Crystals, 2017, vol. 648, # 1, p. 114 - 129
[5] Archiv der Pharmazie, 2017, vol. 350, # 5,
