Synthesis
The general procedure for the synthesis of 2,4-dimethoxybenzyl alcohol from 2,4-dimethoxybenzaldehyde was as follows: to an oven-dried pressure tube equipped with a Teflon-coated stirring bar were added sequentially Pd(OAc)2 (11.2 mg, 5 mol%), PCy3 (21 mg, 7.5 mol%) and 2,4-dimethoxybenzaldehyde (1 mmol). The reaction tube was sealed, evacuated and backfilled three times with nitrogen. Subsequently, 1 mL of dioxane was injected and the mixture was stirred at room temperature for 15 min. H2O (180 mg, 10 eq.) and HCO2H (184 mg, 4 eq.) were then injected and the reaction mixture was heated to 90 °C and kept for 18 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was purified by silica gel fast column chromatography to afford 87 mg of 2,4-dimethoxybenzyl alcohol in 81% yield.
References
[1] Synthetic Communications, 2001, vol. 31, # 17, p. 2719 - 2725
[2] Organic Letters, 2015, vol. 17, # 3, p. 434 - 437
[3] Tetrahedron Letters, 1992, vol. 33, # 37, p. 5417 - 5418
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 182 - 183
[5] Tetrahedron Letters, 1994, vol. 35, # 1, p. 65 - 68
