4-(Diethoxymethyl)benzaldehyde → 4-(Hydroxymethyl)benzaldehyde

Temperature

0 °C

To a cold (0° C.) solution of 4-(diethyoxymethyl)benzaldehyde (5.2 g, 24 mmol) in MeOH (50 mL) was added NaBH4 (0.93 g, 24 mmol), and the reaction mixture was stirred for 3 hours. The MeOH was removed and the residue was taken up in DCM and diluted with water. The aqueous layer was extracted with DCM (3×50 mL). The combine organic layers were dried, filtered and concentrated. The crude oil was dissolved in MeOH (50 mL) and cooled to 0° C. To this was added 2N HCl (10.0 mL) in ether. The reaction mixture was left at room temperature for 24 hours. The MeOH was removed and the crude product was purified by flash column chromatography, eluting with EtOAc/Hexane (3:7) to yield 2.92 g of 4-(hydroxymethyl)benzaldehyde (11) as a colorless oil.

1. customThe MeOH was removed
2. additiondiluted with water
3. extractionThe aqueous layer was extracted with DCM (3×50 mL)
4. customThe combine organic layers were dried
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crude oil was dissolved in MeOH (50 mL)
8. additionTo this was added 2N HCl (10.0 mL) in ether
9. waitThe reaction mixture was left at room temperature for 24 hours
10. customThe MeOH was removed
11. customthe crude product was purified by flash column chromatography
12. washeluting with EtOAc/Hexane (3:7)

ORD record

ord-ee732d22252346e6b92541f5244d0cef

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566716B2