Dichloroacetic Acid → HCID 13076901, compound

Temperature

60 °C

To a suspension of 1.6 g of NaH (60% dispersion in mineral oil) and 131 mg of 18-crown-6 ether in 60 ml of anhydrous dioxane, a solution of 16.4 ml of a solution of dichloroacetic acid (1 M) in anhydrous dioxane was slowly added at room temperature. The reaction mixture was heated to 60° C. and a solution of 3.2 g of 4-Chloro-2-(dicyclohexyl-hydroxy-methyl)-phenol in 42 ml anhydrous dioxane was added and stirred at 90° C. for 6 h. After cooling to 0° C., the reaction mixture was quenched with 8 ml of isopropanol and poured on ice. The aqueous phase was extracted with ether, then acidified with HCl (2 M, to pH 1), and extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was recrystallized from n-heptane to yield a bright yellow product. Yield: 2.5 g.

1. temperatureAfter cooling to 0° C.
2. customthe reaction mixture was quenched with 8 ml of isopropanol
3. additionpoured on ice
4. extractionThe aqueous phase was extracted with ether
5. extractionextracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was recrystallized from n-heptane
10. customto yield a bright yellow product

ORD record

ord-e73b54e6d91949ccb8459958a571b2fb

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221784B2