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Crude 3-(propyloxy)-4-methoxybenzaldehyde (2.60 g) was dissolved in EtOH (30 mL) and cooled to 0° C. NaBH4 (0.499 g, 13.2 mmol) was added portionwise. After the addition was completed, the ice-water bath was removed and the reaction mixture was stirred at room temperature for 2 hours. Water (50 mL) was added and the resulting mixture was extracted with diethyl ether (3×100 mL). The combined organic layers were dried over anhydrous MgSO4. Removal of the solvent gave a pale yellow oil which was purified by silica gel column chromatography (hexanes/EtOAc, 4:1) to give 3-(propyloxy)-4-methoxybenzyl alcohol (2.29 g, 89% over two steps) as a colorless oil.

1. additionAfter the addition
2. customthe ice-water bath was removed
3. additionWater (50 mL) was added
4. extractionthe resulting mixture was extracted with diethyl ether (3×100 mL)
5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
6. customRemoval of the solvent
7. customgave a pale yellow oil which
8. customwas purified by silica gel column chromatography (hexanes/EtOAc, 4:1)