2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

Temperatur

60 °C

A solution of 2,4-dihydroxy-benzaldehyde (101 g, 0.731 mol) in acetonitrile (700 mL) is treated with KI (12.1 g, 73.1 mmol) and NaHCO3 (70.0 g, 0.834 mol). The mixture is stirred while heating to 60° C. Benzyl chloride (120 g, 0.950 mol) is added and the mixture is refluxed at 82° C. for 16 hours and cooled to room temperature. The solvent is evaporated and the reaction is quenched with water (250 mL) and HCl (5.0 N, 30 mL). The mixture is extracted with EtOAc (300 mL×2), and the organic layers is dried over Na2SO4, filtered, and concentrated to an approximate volume of 200 mL. To 400 mL hexanes is added and the resulting solution is heated to 60° C. to dissolve. The solution is cooled to room temperature and crystallized for 16 hours The solid is filtered and dried to obtain the title compound (130 g, 78%). LC-ES/MS m/e 227.0 (M−1).

1. temperaturethe mixture is refluxed at 82° C. for 16 hours
2. temperaturecooled to room temperature
3. customThe solvent is evaporated
4. customthe reaction is quenched with water (250 mL) and HCl (5.0 N, 30 mL)
5. extractionThe mixture is extracted with EtOAc (300 mL×2)
6. dry with materialthe organic layers is dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to an approximate volume of 200 mL
9. additionTo 400 mL hexanes is added
10. temperaturethe resulting solution is heated to 60° C.
11. dissolutionto dissolve
12. temperatureThe solution is cooled to room temperature
13. customcrystallized for 16 hours The solid
14. filtrationis filtered
15. customdried

ORD-Eintrag

ord-eb1e43ac413b45c58d2607d245d5ee2f

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07863302B2