CS269563B1 - 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones; - Google Patents

Abstract

The solution relates to new 3-cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the general formula I, in which R1 represents alkyl with . 2 1 to 2 carbon atoms and R represents cycloalkyl with 5 to 6 carbon atoms, as well as methods of preparation by reacting the corresponding 4-hydroxy3-chloromethylphenylalkyl ketones II with the corresponding alcohol III in a sodium bicarbonate environment at a temperature of 30 to 50 ° C. Compounds of this type can be used as starting materials for the preparation of biologically active substances.

Description

The invention relates to 3-cycloalkoxymethyl-*-hydroxymethylalkyl ketones of the general formula I tm

'2 where R is alkyl having 1 to 2 carbon atoms, R is cycloalkyl having 5 to 6 carbon atoms.

Substances of general formula I are derivatives of p-hydroxyacetophenone or p-hydroxypropiophenone, which are used in the preparation of substances with biological properties (in the preparation of beta-adrenolytic agents, antiarrhythmics, local anesthetics)

3-Cycloalkoxymethyl-4-hydroxyphenylalkyl ketones of the general formula I can be prepared according to the invention by allowing the corresponding 3-chloromethyl-4-hydroxyphenylalkyl ketones of the general formula II, prepared according to the literature Trave R., Gazz. Chim. Ital. 01,773 /1951/., Sohda S., Masatashi F., Tomazo T.,. Norujasu H., 3. Med. Chem 22, 279 /1979/

where R ¹ means alkyl with 1 to 2 carbon atoms., to react with the corresponding alcohol of general formula III

R ² - 0 -Η III

O , where R means cycloalkyl with 5 to 6 carbon atoms in the presence of NaHCO^ at a temperature of 30 50 °C.

Further details will emerge from the following method of preparation

Example

3-Cyclohexyloxy-4-hydroxyphenylmethyl ketone

0.14 mol of 4-hydroxy-3-chloromethylphenylmethylketone is dissolved in 150 ml of cyclohexanol at laboratory temperature and 0.29 mol of NaHCO 3 is gradually added. The mixture is left to react for 4 hours at room temperature and then heated for 4 hours at a temperature of 30-50°C. After filtering off NaHCO 3 and distilling off cyclohexanol under reduced pressure, the oily residue is crystallized from heptane or hexane.

3-cyclohexyloxy-4-hydroxyphenylmethylketone-white crystalline substance is formed in an extract of 60 i theory, m.p. 61-3°C /hexane/

Analysis calc./found ’t C 72.55 / 72.77 % H 8.12 / 8.05

IČ / cm' ¹ / i _as /C=0/ 1676., < _c=c 1590., ^ _as /C _Ar ° C _A1 / 1250

1h-NMR / d ppm/ ArCH ₂ 0 4.00 /2H,s/., CHjCO 2.50 /3H,s/

O-CH< 3.45 /1H,m/., cyclohexyl 1.5-2.00 /10 H,m/

CS ^: 269563 Bl.

Using the above-mentioned method, the following not yet described substances were prepared: substances i >.. >

1. 3-cyclopentoxy-4-hydroxy phenylmethylketor; > < <t. m.p. 6B-71°C /heptane/

2. 3-cyclopentoxy-4-hydroxyphenylethyl ketones m.p. 68-9°C, /heptane/

3. 3-cyclohexyloxy-4-hydroxyphenylmethyl ketone, m.p. 61-4°0 /hexane/

4. 3-cyclohexyloxy-4-hydroxyphenylethyl ketone, m.p. 54-7°C /hexane/

Claims (2)

OBJECT OF THE FINDING 1. 3-Cycloalkoxymethyl-4-hydroxyphenylalkylketones of general formula I OH Γ0Ρ CH ₂ 0R ² I COR ¹ 1 '2 · where R is alkyl with 1 to 2 carbon atoms and R is cycloalkyl with 5 to 5 carbon atoms 2. Method for the preparation of 3-cycloalkoxymethyl-4-hydroxyphenylalkylketones of the general formula I according to point 1, characterized in that 4-hydroxy-3-chloromethylphenylalkylketones of the general formula II are allowed to react where R means the same as in formula I, with the corresponding alcohol of general formula III R ² - 0 - H . where R ² means the same as in formula I, in the presence of NaHCO 3 at a temperature of 30 - 50 °C.