Patent / 1964
Instituto Pasteur de Lisboa
Substituted .alpha.-ketols (I) with cortico-adrenal activity were prepd. by the reaction of substituted phenylbromopropanes with .alpha.-phenylacetol (II). Thus, I (R1 = OH, R2 = OMe, R3 = H) was obtained by treating 15 g. II in 80 ml. abs. Et2O with 5.4 g. NaOMe 3 hrs. at -5 to 0.degree., 24.5 g. bromoeugenol in 80 ml. Et2O added, the mixt. stirred 6 hrs. at ambient temp. then refluxed 2 3 hrs., pH adjusted with H3PO4 to 6-6.5, NaBr filtered off, the Et2O evapd., and the product isolated by dissolving in hot HOAc and pptg. with H2O. Other I were similarly prepd. by reaction of II with bromoanethole (R1 = OMe, R2 = H, R3 = H), with bromoisosafrol [(R1R2 =) OCH2O2, R3 = H], and with bromocinnamyl alc. (R1 = H, R2 = H, R3 = OH).