4-Hydroxybenzaldehyde → 4-(2,2-Diethoxyethoxy)benzaldehyde

Temperatur

27.5 °C

To a stirred suspension of sodium hydride (2.5 g, 100 mmol, 98%) in DMF (100 mL) was added a solution of 4-hydroxy benzaldehyde (10.0 g, 82 mmol) in DMF (100 mL) slowly dropwise at 25-30° C. and stirred for 30 min at 25-30° C. 2,2-diethoxy-1-bromoethane (19.7 g, 100 mmol) was added to the reaction mixture. The reaction mixture was immersed in a preheated oil bath at 60° C. and stirring was continued for 48 h at 60° C. The reaction mixture was cooled to room temperatures, quenched with water (200 mL) and extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography using EtOAc:pet. ether (1:2) as eluent to yield the title compound (12.65 g, 58%) as a brown coloured liquid.

1. customThe reaction mixture was immersed in a preheated oil bath at 60° C.
2. stirringstirring
3. waitwas continued for 48 h at 60° C
4. temperatureThe reaction mixture was cooled to room temperatures
5. customquenched with water (200 mL)
6. extractionextracted with ethyl acetate (3×300 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated
10. customThe crude compound was purified by column chromatography

ORD-Eintrag

ord-630ac9edad534ff9ba05c78643ac3bd2

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06313113B1