Reaktion #9724

Reaktionsgleichung

hydrochloric acid

ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate

intermediate 9

ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate

sodium ethoxide

→

title compound

ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe solution concentrated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in t-butylmethyl ether
3. 3
   Waschenthe resulting solution washed with water
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenthe filtrate concentrated
7. 7
   Sonstigeto give a brown oil
8. 8
   SonstigeFurther purification by Biotage® chromatography
9. 9
   Wascheneluting initially with cyclohexane

Vorschrift

A solution of ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate (intermediate 9, 40.8 g) in ethanol (280 ml) was treated with sodium ethoxide (12.9 g) at room temperature under nitrogen. The resulting solution was heated to 50° C. for 1 hour. 2M hydrochloric acid (95 ml) was added to the cooled reaction and the solution concentrated. The residue was dissolved in t-butylmethyl ether and the resulting solution washed with water followed by brine and then dried over sodium sulfate, filtered and the filtrate concentrated to give a brown oil. Further purification by Biotage® chromatography eluting initially with cyclohexane and then cyclohexane:ethyl acetate (5:1) gave the title compound as an orange oil.

Quelle