Hydrochloric Acid → HCID 85077994, compound

Temperature

-65 °C

Butyllithium (50 mL of 2.5 N solution) was added to 250 mL of anhydrous tetrahydrofuran (THF) at −65° C. A solution of diethylphosphonoacetic acid (11.4 g) in 90 mL of anhydrous THF was added dropwise to the stirred solution at −65° C. The resulting solution was stirred at −65° C. for an additional 40 minutes and then a solution of α-chloro-cinnamaldehyde (10.0 g) in 60 mL of anhydrous THF was added to the reaction at −65° C. over a period of 95 minutes. The reaction was stirred for one hour, allowed to warm to room temperature and then stirred overnight. The reaction was then acidified with 5% hydrochloric acid (48 mL) to a pH of 3.9. The aqueous layer was extracted with 50 mL of ether twice and with 50 mL of ethyl acetate once. The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude material was dissolved in 30 mL of hot methanol and then refrigerated overnight. The crystals formed were filtered and dried under vacuum to afford 9.2 g of the desired 4-chloro-5-phenyl-2,4-pentadienoic acid. 1H NMR (acetone-d6, 300 MHz), δ(ppm) 7.86 (d, 2H), 7.60 (d, 1H), 7.45 (m, 3H), 7.36 (broad s, 1H), 6.32 (d, 1H).

1. stirringThe reaction was stirred for one hour
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. extractionThe aqueous layer was extracted with 50 mL of ether twice
5. extractionThe combined organic extract
6. dry with materialwas dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. dissolutionThe crude material was dissolved in 30 mL of hot methanol
10. customrefrigerated overnight
11. customThe crystals formed
12. filtrationwere filtered
13. customdried under vacuum

ORD record

ord-d196e8b304364c3ca1be339038d89a6c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842727B2