Phosphorus oxychloride → 3-Methyl-5-phenyl-2,4-pentadienoic acid

Dimethylformamide (DMF, anhydrous, 25 mL) was cooled to 0-5° C. and phosphorus oxychloride (16.4 mL) was added dropwise over a period of an hour. The resulting solution was added dropwise to a cooled (0-5° C.) solution of 4-phenyl-2-methyl-3-buten-2-ol (0.14 mol) in 60 mL of anhydrous DMF over a period of an hour. The reaction mixture was then warmed to room temperature, gradually heated up to 80° C., stirred at 80° C. for three hours and cooled to 0-5° C. To the cooled reaction solution was added dropwise a solution of sodium acetate (80 g) in deionized water (190 mL) over a period of two hours. The mixture was then reheated to 80° C., stirred at 80° C. for an additional 10 minutes, cooled down to room temperature and extracted with ether (300 mL) twice. The combined extract was washed with water (200 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to yield 16.7 g of the desired 3-methyl-5-phenyl-2,4-pentadienal as a liquid which was used in the next step without further purification.

1. additionThe resulting solution was added dropwise to
2. temperaturegradually heated up to 80° C.
3. temperaturecooled to 0-5° C
4. customTo the cooled reaction solution
5. customwas then reheated to 80° C.
6. stirringstirred at 80° C. for an additional 10 minutes
7. temperaturecooled down to room temperature
8. extractionextracted with ether (300 mL) twice
9. extractionThe combined extract
10. washwas washed with water (200 mL)
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuum

ORD-Eintrag

ord-607190d3a7f8493cb166b904c9a6fb2f

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08026280B2