Hydrochloric Acid → 4-(2-Hydroxyethyl)benzaldehyde

Temperature

60 °C

Next, a mixture of 4-(2-methoxymethoxyethyl)benzaldehyde (8.2 g, 42.1 mmol), methanol (160 mL), water (6 mL) and concentrated hydrochloric acid (4 mL) was stirred at 60° C. for 17.5 hours. After cooling to room temperature, the reaction mixture was neutralized with aqueous sodium hydroxide and evaporated under reduced pressure to remove methanol. The residue was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After concentration, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50) to give 4-(2-hydroxyethyl)benzaldehyde (6.3 g).

1. temperatureAfter cooling to room temperature
2. customevaporated under reduced pressure
3. customto remove methanol
4. extractionThe residue was extracted twice with ethyl acetate
5. washThe combined organic layers were washed with saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationAfter concentration
8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50)

ORD record

ord-0aa31944b4b44a2b80329b50f489be99

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439232B2