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

Temperature

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 record

ord-630ac9edad534ff9ba05c78643ac3bd2

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313113B1