2-Chloroethanol → HCID 59205673, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 13 grams (0.048 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound), 6.8 grams (0.048 mole) of potassium carbonate and 3.9 grams (0.048 mole) of 2-chloroethanol in 80 mL of DMF was heated to 70° C. where it stirred for three hours. After this time the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with 100 mL of aqueous 10% hydrochloric acid then extracted with three 150 mL portions of ethyl acetate. The combined extracts were washed with an aqueous saturated sodium chloride solution, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The crude residue was purified with column chromatography on silica gel using 6:4 heptane:ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 10.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence