CS269563B1 - 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones and method of their production - Google Patents

Abstract

The present invention relates to novel 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of of formula I wherein R 1 is alkyl s . 2 With 1 to 2 carbon atoms and R is cycloalkyl with 5 to 6 carbon atoms and methods by the reaction of the corresponding 4-hydroxy-3-chloromethylphenylalkyl ketones II with relevant alcohol III in bicarbonate sodium at 30-50 ° C. Compounds of this type can be used as starting materials raw materials for biological preparation active substances.

Description

CS 269563 B1 1

The present invention relates to 3-cycloalkoxymethyl-4-hydroxy-methyl-alkyl ketones of formula (I)

Wherein R is alkyl of 1 to 2 carbon atoms, R is cycloalkyl of 5 to 6 carbon atoms. The compounds of formula (I) are derivatives of β-hydroxyacetophenone, respectively. The p-hydroxypropionphenone used in the preparation of substances with biological properties (in the preparation, beta-adrenolytics, antiarrhythmic agents, local anesthetics) of the 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the formula I can be prepared by leaving the corresponding 3 chloromethyl-4-hydroxyphenylalkyl ketones of general formula II, prepared according to the literature of Travé R., Gazz. Chim. Italian. 01,773 (1951), Sohda, S., Masatashi, F., Tomazo, T.,. Norujasu H., 3. Hed. Chem 22, 279 (1979)

. OH fm " C "

wherein R 1 is C 1 -C 2 alkyl, reacting with the appropriate alcohol of formula III

R 2 -O-III O, wherein R is C 5 -C 6 cycloalkyl in the presence of NaHCO 3 at 30-50 ° C.

For more details, please refer to the following procedure. Example 3-Cyclohexyloxy-4-hydroxyphenylmethylketone 0.14 mol 4-Hydroxy-3-chloromethylphenylmethyl ketone is dissolved in 150 ml cyclohexanol at room temperature and 0.29 mol NaHCO 3 is added sequentially. The mixture is reacted at room temperature for 4 hours and then heated at 30-50 ° C for 4 hours. After filtering off the NaHCO3 and distilling off the cyclohexanol under reduced pressure, the oily residue crystallized from heptane and heptane respectively. hexane. The 3-cyclohexyloxy-4-hydroxyphenylmethylketone-white crystalline solid is formed in 60% yield, m.p. 61-3 ° C / hexane /

Analysis calculated / found C 72.55 / 72.77 · -. H 8.12 (8.05 IR / cm @ -1), [.alpha.] D @ 20/1676. 80 (2H, s), CH 2 CO 2,50 / 3H, s / O-CH < = 3.45 (1H, m), cyclohexyl 1.5-2.00 / 10H, m / s;

Claims (2)

CS: 269563 Bl. Using the above-mentioned method, the sleds have not been drank so far! a compound of formula (I); 3-cyclopentoxy-4-hydroxyphenylmethylkeiter; i í <t. 60-71 ° C / heptane / 2. 3-Cyclopentoxy-4-hydroxyphenylethylketones m.p. 68-9 ° C, [heptane / 3. 3-cyclohexyloxy-4-hydroxyphenylmethyl ketone, m.p. 61-4 ° C / hexane / 4-3-cyclohexyloxy-4-hydroxyphenyl ethyl ketone, m.p. 54-7 ° C / Hexane / RREDHET VY LEZU 1. 3-Cycloalkoxymethyl-4-hydroxyphenylalkylketones of Formula IOH Ί COR1-1 where R is alkyl of 1 to 2 carbon atoms and R is cycloalkyl of 5 to carbon atoms 2. Process for the preparation of 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the formula I according to claim 1, characterized in that 4-hydroxy-3-chloromethylphenyl alkyl ketones of the formula II are reacted. COR 2 wherein R is the same as in Formula I, with the appropriate alcohol of Formula III wherein R 1 is the same as in Formula I, in the presence of NaHCO 3 at 30-50 ° C.